(Trifluoromethyl)trimethylsilane → HCID 59463781, compound

Participants

Reaction Steps

To 383 mg (1.6 mmol) of (4-methyl-6-methylsulfanylchroman-4-yl)acetaldehyde and 0.335 mL (1.4 mmol) of trimethyl(trifluoromethyl)silane in 5 mL of tetrahydrofuran was added 3 drops of a 1 M solution of tetrabutylammonium fluoride in tetrahydrofuran. The mixture stirred for 1 hour and then an additional 1.8 mL (1.8 mmol) of a 1 M solution of tetrabutylammonium fluoride in tetrahydrofuran was added. After 18 hours, the mixture was concentrated in vacuo and diluted with 1N aqueous HCl and extracted with three 50 mL portions of diethyl ether. The combined organic layers were dried over magnesium sulfate, filtered, and concentrated in vacuo to afford 0.45 g of 1,1,1-trifluoro-3-(4-methyl-6-methylsulfanylchroman-4-yl)propan-2-ol as a mixture of diastereomers. The crude oil was used without further purification.

Provenance & Evidence