Reaction #1885039

Reaction equation

(S)-3-hydroxydihydrofuran-2(3H)-one

imidazole

THF

t-butyldiphenylsilyl chloride

→

(S)-3-(tert-butyldiphenylsilyloxy)dihydrofuran-2(3H)-one

Yield 95.0%

Solvents

TBME

Conditions

Workup

1. 1
   Washthe solution was washed with water (2×100 mL), brine (100 mL)
2. 2
   Dryingdried over sodium sulfate
3. 3
   Filtrationfiltered
4. 4
   Otherevaporated to dryness under reduced pressure

Procedure

To a stirred solution of (S)-3-hydroxydihydrofuran-2(3H)-one (5.24 g, 51.4 mmol), imidazole (3.8 g, 56 mmol), and THF (70 mL) at 0° C., under N2, was added t-butyldiphenylsilyl chloride (11.8 g, 43 mmol) dropwise. The mixture was stirred at 0° C. for 6 hours. TBME (150 mL) was added and the solution was washed with water (2×100 mL), brine (100 mL), dried over sodium sulfate, filtered, and evaporated to dryness under reduced pressure to afford (S)-3-(tert-butyldiphenylsilyloxy)dihydrofuran-2(3H)-one (13.9 g, 95%) as a slightly yellow oil. 1H-NMR (400 MHz, CDCl3) δ 7.84-0.82 (m, 2H), 7.73-7.71 (m, 2H), 7.50-7.40 (m, 6H), 4.41-4.31 (m, 2H), 4.06-4.00 (m, 1H), 2.29-2.19 (m, 2H), 1.10 (s, 9H).

Source