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

Boiling point:

67-68 °C(Press: 14 Torr)

Density 

0.868±0.06 g/cm3(Predicted)

InChI

InChI=1S/C9H20O2Si/c1-8(7-10)11-12(5,6)9(2,3)4/h7-8H,1-6H3/t8-/m0/s1

InChIKey

YMIIHJBTQLZXBV-QMMMGPOBSA-N

SMILES

C(=O)[C@@H](O[Si](C(C)(C)C)(C)C)C

(S)-2-(tert-Butyldimethylsilyloxy)propanal Usage And Synthesis

storage

Inert atmosphere,Store in freezer, under -20C

Synthesis

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.