All reagents were obtained from commercial sources and used without further purification. Dry THF, MeOH, DCM, and DMF were obtained from Sigma-Aldrich (St. Louis, MO). 1H and 13C NMR spectra were recorded at 23°C on a Bruker 400 MHz spectrometer. Recorded shifts are reported in parts per million (δ) and calibrated using residual undeuterated solvent. Data are represented as follows: chemical shift, multiplicity (s = singlet, d = doublet, t = triplet, q = quartet, p = pentet, m = multiplet, br = broad), coupling constant (J, Hz), and integration. LC-ESI-MS analysis and HPLC-purifications were performed on a Waters (Milford, MA) LC-MS system. For LC-ESI-MS analyses, a Waters XTerra® C18 5 μm column was used. For preparative runs, an Atlantis® Prep T3 OBDTM 5 μm column was used [eluents 0.1% TFA (v/v) in water (solution A) and MeCN (solution B); gradient: 0–1.5 min, 5–100% B; 1.5–2.0 min, 100% B for analysis and 0–0.75 min, 5% B; 0.75–9.0 min, 5–100% B; 9.0–10.0 min, 100% B for prep.].
Dry thf
Manufactured by Merck Group
Dry THF is a solvent product offered by Merck Group. It is a clear, colorless liquid that is used in various chemical and laboratory applications. The core function of Dry THF is to provide a low-water, high-purity solvent for reactions and other processes that require a dry, aprotic environment.
Automatically generated - may contain errors
Lab products found in correlation
Xterra c 18 5 μm column, by Waters Corporation (1 mentions)
400 mhz spectrometer, by Bruker (1 mentions)
N n dimethylformamide (dmf), by Merck Group (1 mentions)
Lc ms system, by Waters Corporation (1 mentions)
Concentrated hydrochloric acid, by Avantor (1 mentions)
Cdcl3, by Eurisotop (1 mentions)
Glacial acetic acid, by Avantor (1 mentions)
Triethylamine, by Thermo Fisher Scientific (1 mentions)
Aluminum chloride, by Merck Group (1 mentions)
2 aminoterephthalic acid, by Merck Group (1 mentions)
Acetyl chloride, by Thermo Fisher Scientific (1 mentions)
Dry toluene, by Thermo Fisher Scientific (1 mentions)
3 protocols using dry thf
1
Purification and Characterization of Compounds
2
Synthesis of Functionalized Organic Compounds
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(TiCl3)3AlCl3 (76.0–78.5% TiCl3) and acetyl
chloride (98%) were purchased from Alfa Aesar. Dry toluene (99.85%,
extra dry, AcroSeal), 4-bromoacetophenone (98%), potassium pyrosulfate
(98%), n-BuLi (1.6 M in hexanes), and 2,4,6-trimethylaniline
(97%) were purchased from Acros Organics. Dry THF (≥99.9%,
with 250 ppm of butylated hydroxytoluene (BHT) as an inhibitor), aluminum
chloride (99.9%), and 2-aminoterephthalic acid (99%) were purchased
from Sigma-Aldrich. DMF (HiPerSolv, CHROMANORM), dichloromethane (DCM)
(HiPerSolv, CHROMANORM), sulfuric acid (96%), chloroform (HiPerSolv,
CHROMANORM), concentrated hydrochloric acid (37%), glacial acetic
acid (ACS reagent grade), and ethanol (technical grade) were purchased
from VWR. The acetone used was of technical grade. Triethylamine (99.7%)
was purchased from Fisher Chemicals. CDCl3, NaOD (40% w/w
in D2O, ≥99.00%), and D2O were purchased
from Eurisotop. Carbon dioxide (Alphagaz 1) was purchased from Air
Liquide. Potassium permanganate crystals were purchased from J.T.
Baker Chemicals N.V. (Holland).
chloride (98%) were purchased from Alfa Aesar. Dry toluene (99.85%,
extra dry, AcroSeal), 4-bromoacetophenone (98%), potassium pyrosulfate
(98%), n-BuLi (1.6 M in hexanes), and 2,4,6-trimethylaniline
(97%) were purchased from Acros Organics. Dry THF (≥99.9%,
with 250 ppm of butylated hydroxytoluene (BHT) as an inhibitor), aluminum
chloride (99.9%), and 2-aminoterephthalic acid (99%) were purchased
from Sigma-Aldrich. DMF (HiPerSolv, CHROMANORM), dichloromethane (DCM)
(HiPerSolv, CHROMANORM), sulfuric acid (96%), chloroform (HiPerSolv,
CHROMANORM), concentrated hydrochloric acid (37%), glacial acetic
acid (ACS reagent grade), and ethanol (technical grade) were purchased
from VWR. The acetone used was of technical grade. Triethylamine (99.7%)
was purchased from Fisher Chemicals. CDCl3, NaOD (40% w/w
in D2O, ≥99.00%), and D2O were purchased
from Eurisotop. Carbon dioxide (Alphagaz 1) was purchased from Air
Liquide. Potassium permanganate crystals were purchased from J.T.
Baker Chemicals N.V. (Holland).
3
Synthesis of Bromoalkane-Substituted Roy Compound
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A bromoalkane was coupled to Roy by SN2 substitution. NaH (60% in mineral oil, 1.068 mg, 3 Eq, Sigma) was suspended in dry THF (1.5 mL, Sigma) in a three-necked flask, at 0 °C, and under argon atmosphere. A solution of Roy (10 mg, 1 eq) in dry THF was added dropwise, keeping the temperature below 0 °C. The reaction mixture was stirred for 30 min at 0 °C and then for 20 min 25 at ambient temperature. After cooling again to 0 °C, a solution of 1-bromododecane (17.82 µL, 3 eq) in dry THF (1 mL) was slowly added. The mixture was stirred at ambient temperature overnight, heated on steam. (Scheme 2 ).
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