Ethyl (S)-(-)-2-(tert-butyldimethylsilyloxy)propionate → (S)-2-(tert-Butyl-dimethyl-silanyloxy)-propan-1-ol

Diisobutylaluminum hydride (1M in DCM) (41.4 mL, 41.42 mmol) was added dropwise to a stirred solution of (S)-ethyl 2-(tert-butyldimethylsilyloxy)propanoate (CAS no. 106513-42-2) (5 mL, 18.83 mmol) in diethyl ether (25 mL) at ˜78° C. under nitrogen. The resulting mixture was stirred at r.t. for 2 hours. The reaction mixture was carefully quenched with 20% Rochelle's solution (>100 ml) and at −78° C. and allowed to warm to r.t. After 2 hours of vigourous stirring the mixture was extracted with Et2O ×2, the organic layer was dried (MgSO4), filtered and evaporated to afford colourless liquid, (S)-2-(tert-butyldimethylsilyloxy)propan-1-ol (3.50 g, 98%). 1H NMR (400 MHz, CDCl3) δ 0.00 (6H, s), 0.81 (9H, s), 1.03 (3H, d), 1.71-1.90 (1H, m), 3.24-3.33 (1H, m), 3.35-3.44 (1H, m), 3.78-3.87 (1H, m).

1. customat ˜78° C.
2. customThe reaction mixture was carefully quenched with 20% Rochelle's solution (>100 ml) and at −78° C.
3. temperatureto warm to r.t
4. stirringAfter 2 hours of vigourous stirring the mixture
5. extractionwas extracted with Et2O ×2
6. dry with materialthe organic layer was dried (MgSO4)
7. filtrationfiltered
8. customevaporated

ORD record

ord-031fabc5114f47ccb6762b3176c03eea

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08143263B2