Dichloromethane → HCID 10867393, compound

To a 50 ml round bottom flask was introduced 200 mg (0.86 mmol) of methyl (S)-3-t-butyldimethylsilyloxybutanoate, to which was added 2.5 ml dry CH2Cl2. The reaction was stirred in a dry ice/acetone bath, and 1.72 ml (2 eq.) of 1M diisobutylaluminum hydride in toluene was added dropwise. After stirring for 1 hour at -78° C., the reaction was quenched with 2 ml of MeOH and warmed to room temperature. The reaction was diluted with 25 ml of CH2Cl2 and 8 ml saturated aq. potassium sodium tartrate was added. The organic layer was separated and dried over MgSO4 and the solvent was removed under reduced pressure. Thin layer chromatography using 10% ethyl acetate in hexane showed complete and clean conversion to a lower Rf spot. This afforded 170 mg (98%) of the product, (S)-3-t-butyldimethylsilyloxybutanal, which was used without purification to avoid racemization.

1. stirringAfter stirring for 1 hour at -78° C.
2. customthe reaction was quenched with 2 ml of MeOH
3. additionThe reaction was diluted with 25 ml of CH2Cl2 and 8 ml saturated aq. potassium sodium tartrate
4. additionwas added
5. customThe organic layer was separated
6. dry with materialdried over MgSO4
7. customthe solvent was removed under reduced pressure
8. customThis afforded 170 mg (98%) of the product, (S)-3-t-butyldimethylsilyloxybutanal, which was used without purification

ORD record

ord-fe81c1b468aa4b5a9f0bf4c2d2ab9717

Source dataset

uspto-grants-1994_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05332807