Chloroester 11b was prepared according to a previously reported procedure.30 Ethyl chloroformate (22 , 2.86 mL, 30.0 mmol, 3.00 equiv), 1-heptyne (21b , 1.31 mL, 10.0 mmol, 1.00 equiv, Sigma-Aldrich), and bis(triphenylphosphine)rhodium(I) carbonyl chloride (69.0 mg, 0.10 mmol, 0.01 equiv) were dissolved in 6 mL of dry toluene in a sealed container and heated to 110 °C for 24 h. The reaction mixture was cooled to room temperature, quenched by the addition of sat. aqueous NaHCO3, and extracted 3× with EtOAc. Organics were dried with Na2SO4, filtered, and concentrated in vacuo. Flash column chromatography on silica using a gradient of 0–20% EtOAc in hexanes afforded 11b (1.93 g, 94%) as a light yellow oil. 1H NMR (500 MHz, benzene-d6): δ 5.85 (t, J = 1.0 Hz, 1H), 4.01 (q, J = 7.1 Hz, 2H), 1.97 (t, J = 7.6 Hz, 2H), 1.29 (p, J = 7.6 Hz, 2H), 1.13–1.02 (m, 2H 1.00–0.92 (m, 2H), 0.98 (t, J = 7.1 Hz, 3H), 0.76 (t, J = 7.3 Hz, 3H). 13C{1H} NMR (126 MHz, benzene-d6): δ 163.5, 150.2, 116.9, 60.2, 41.2, 30.8, 27.0, 22.6, 14.3, 14.0. HRMS (ESI) m/z: [M + H]+ calcd for C10H18ClO2, 205.0990; found, 205.0987.
1 heptyne
Manufactured by Merck Group
Sourced in Japan
1-heptyne is a linear alkyne compound with the chemical formula C7H12. It is a colorless, volatile liquid with a characteristic odor. 1-heptyne is commonly used as a chemical building block and as a versatile intermediate in organic synthesis. No further details on intended use can be provided in an unbiased and factual manner.
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3 protocols using 1 heptyne
1
Synthesis of Chloroester 11b
2
Characterization of Linear 1-Alkynes
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Phenylacetylene (98%) and propyne, 1-pentyne, 1-hexyne, 1-heptyne, and 1-octyne (C3, C5, C6, C7, and C8 linear 1-alkynes, respectively, ≥97%) were obtained from Sigma-Aldrich. 1-Butyne was supplied by Apollo Gases Ltd. Acetylene was obtained from BOC, a member of the Linde Group. Protein concentrations were determined using a Pierce bicinchoninic acid (BCA) protein assay kit (Thermo Scientific) as described by the manufacturer.
3
Extraction and Characterization of Sargassum thunbergii
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The brown alga Sargassum thunbergii was collected in Aio bay in Yamaguchi prefecture, Japan in December, 2015. The alga samples were stored at -20℃ until use. 2-Propyn-1-ol and trimethylsilylacetylene were purchased from Kanto Chemical Co. (Tokyo, Japan) . 2-Pentyn-1-ol was purchased from Tokyo Chemical Industry Co. (Tokyo, Japan) . 1-Heptyne was purchased from Sigma-Aldrich Co. (Tokyo, Japan) . All other chemicals and solvents were commercially of the highest grade.
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