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3 protocols using t butanol

1

Steroid Synthesis and Characterization

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All chemicals, reagents, and solvents used
in this synthesis were of reagent grade or better and were inspected
and released for use based on the manufacturer’s Certificates
of Analysis. Prednisolone was from Steraloids, deuterium gas was from
Cambridge Isotopes, Wilkinson’s catalyst was from Combi-Chem,
sodium borohydride was from Oakwood, t-butanol was
from Alfa Aesar, anhydrous dioxane, toluene, dichloromethane, methanol,
and deuterated methanol were from Acros, and all remaining chemicals
and solvents were from Sigma-Aldrich. HPLC analyses used HPLC-grade
acetonitrile (Fisher), HPLC-grade ammonium acetate (Fisher), and deionized
water. For high-resolution LC–MS, water and acetonitrile were
from Fisher (Optima LC/MS grade); ammonium acetate was from Fluka
(LC–MS ultra grade).
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2

On-Resin Triazolyl Cross-Link Formation

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The 1,4-disubstituted-[1 (link),2 (link),3 (link)]-triazolyl cross-link was formed on-resin using copper(I)-catalyzed azide-alkyne cycloaddition chemistry. The resin (25 μmol) was suspended in a 1:2 solution of t-butanol (Alfa Aesar) and water. Sodium ascorbate (160 mg, 750 μmol, 30 equiv.) and copper sulfate (55 mg, 375 μmol, 15 equiv.) were added, causing the mixture to turn bright orange. The mixture was left to stir overnight. The mixture was then returned to a synthesis column, washed with 1:2 solution of t-butanol/water, and dried for a test cleavage. Cyclization was confirmed by a shift in retention time using LC/MS.
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3

Synthesis and Characterization of Organic Compounds

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2-propanol-d8 (99%), KBr (99.95%), (E)-benzalacetone, (E)-4-(furan-2-yl)but-3-en-2-one (98.0%), 1,3-diphenyl-propen-3-one (97%), 1-propenylbenzene (96%), 4-phenyl-1-butene were acquired from Shanghai Aladdin Biochemical Technology Co., Ltd. 2-methylimidazole (99%), 1-propanol (99.5%), (E)-3-(2-furanyl)-2-propenal (98%), cinnamyl alcohol (98%) were purchased from J&K Scientific Ltd. Methanol (99.7%), ethanol (99.7%), 2-propanol (99.8%), pyridine (99.5%), benzyl alcohol were acquired from Concord Technology (Tianjin) Co., Ltd. KSCN (99.5%), (E)-1-phenyl-1-butene (97%), triphenylmethane (99%), cinnamaldehyde (98%) were purchased from Shanghai Macklin Biochemical Co., Ltd. 1-butanol (99.5%), triphenylMethanol (99%),dodecane (99%), boric acid (99.5%), Zn(NO3)2·6H2O, propylbenzene (99%), allylbenzene (98%), chitosan (99%) were acquired from Beijing InnoChem Science & Technology Co., Ltd. Cinnamyl acetate (97%) was acquired from TCI (Shanghai) Development Co., Ltd. 3-phenyl-1-propanol (98%) was purchased from Adamas-Beta. 4-hydroxy-3-methoxycinnamaldehyde (97%) was acquired from Sigma-Aldrich. t-butanol was purchased from Alfa Aesar. Nitrogen (99.99%), argon (99.99%) and hydrogen (99.99%) were provided by Beijing Analytic Instrument Company. All reagents were directly used without further purification.
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