Methanol → (S)-(+)-3-(t-butyldimethylsilyloxy)-2-methylpropanal

Methyl (S)-(+)-3-(t-butyldimethylsilyloxy)-2-methylpropionate (1.31 g; 5.6 mmol) was dissolved in anhydrous ether (18.5 ml), and a hexane solution (8.4 ml) of 1M diisobutylaluminum hydride was added dropwise thereto at -78° C. in 5 minutes in an argon stream. After stirring for 30 minutes, methanol (0.09 ml) and then water (0.84 ml) were added thereto, and the resultant mixture was allowed to stand at room temperature, followed by stirring at the same temperature for 1 hour. The reaction mixture in gel was filtered, dried over anhydrous magnesium sulfate, and the solvent was distilled under reduced pressure. Purification of the oily residue by silica gel column chromatography using a mixture of hexane and ethyl acetate (9:1) gave (S)-(+)-3-(t-butyldimethylsilyloxy)-2-methylpropanal (0.89 g, yield, 78%) as a colorless oil.

1. customto stand at room temperature
2. stirringby stirring at the same temperature for 1 hour
3. filtrationThe reaction mixture in gel was filtered
4. dry with materialdried over anhydrous magnesium sulfate
5. distillationthe solvent was distilled under reduced pressure
6. customPurification of the oily residue by silica gel column chromatography
7. additiona mixture of hexane and ethyl acetate (9:1)

ORD record

ord-7be41f1ece644faf85d11acab5bc8a07

Source dataset

uspto-grants-1990_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04892961