ChemicalBook CAS DataBase List (S)-2-(tert-Butyldimethylsilyloxy)propanal

(S)-2-(tert-Butyldimethylsilyloxy)propanal synthesis

6synthesis methods

Product Name:(S)-2-(tert-Butyldimethylsilyloxy)propanal
CAS Number:87727-28-4
Molecular formula:C9H20O2Si
Molecular Weight:188.34

Ethyl ester 3 (4.00 g, 17.2 mmol) was added to diethyl ether (70 mL) and cooled to -78 °C. DIBAL-H (1M in hexane, 20 mmol, 20 mL) was added cautiously dropwise over 1 h. The solution was stirred for a further 4 h at -78 °C before being quenched with MeOH (40 mL) and warmed to room temperature. Saturated potassium sodium tartrate solution (60 mL) was added and the mixture was left to stir for 12 h before being extracted with diethyl ether (3 x 15 mL). The organic extracts were dried with MgSO4, filtered, and concentrated under reduced pressure to give the crude (S)-2-(tert-Butyldimethylsilyloxy)propanal (3.22 g, 99%) as a clear oil.

(S)-2-(tert-Butyldimethylsilyloxy)propanal

(S)-2-((tert-butyldimethylsilyl)oxy)propan-1-ol

135614-57-2
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87727-28-4
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Yield:87727-28-4 71%

Reaction Conditions:

with oxalyl dichloride;(methylsulfinyl)methane;triethylamine in dichloromethane at -78 - 20; for 2 h;Inert atmosphere;

Steps:

10.3 Step 3: preparation of (S)-2-((tert-butyldimethylsilyl)oxy)propanal (4)

To a solution of (COCI) (27.1 g, 0.21 mol, 1.1 eq) in DCM (400 mL) was added DMSO (36.5 g, 0.46 mol, 2.4 eq) dropwise at -78°C under Ar. After stirring at -78°C for 30 min, a solution of compound 3 (37.0 g, 0.19 mol, 1.0 eq) in DCM (50 mL) was slowly added into the mixture. After stirring at -78°C for 30 min, TEA (98.0 g, 0.97 mol, 5.0 eq) in DCM (50 mL) was slowly added into the mixture. The reaction mixture was stirred at -78°C for 30 min, then warmed to rt for 1 hour. The mixture was quenched with NH4CI aq at -78°C, extracted with DCM, washed with Brine, dried with Na2SC>4, concentrated, and purified by column chromatography (PE/DCM = 200:1) to give compound 4 as a colorless oil (26.0 g, 71% yield).

References:

WO2021/61515,2021,A1 Location in patent:Page/Page column 133; 134