반응 #85656

반응 방정식

(R)-2-((S)-3-benzyl-2-oxooxazolidin-4-yl)-N-methoxy-N-methylpropanamide

DIBAL-H

→

(R)-2-((S)-3-benzyl-2-oxooxazolidin-4-yl)propanal

수율 105.3%

용매

Rochelle's salt

THF

반응 조건

후처리

1. 1
   workup.STIRRINGstirred vigrously for ˜15 min
2. 2
   기타The aqueous layer was separated
3. 3
   추출extracted with ethyl acetate (3×)
4. 4
   세척The combined organic extracts were washed with saturated sodium bicarbonate solution and brine
5. 5
   여과filtered through a mixture of celite/silica gel
6. 6
   농축The filtrate was concentrated under reduced pressure

실험 절차

To a solution of (R)-2-((S)-3-benzyl-2-oxooxazolidin-4-yl)-N-methoxy-N-methylpropanamide from Step 6 (1.5 g, 5.13 mmol) in THF (30 mL) was added dropwise DIBAL-H (1M solution in hexane; 11.29 mL) at −78° C. The mixture was stirred for 90 min at −78° C., diluted slowly with Rochelle's salt solution (1M solution in water; ˜20 mL) and stirred vigrously for ˜15 min. The aqueous layer was separated and extracted with ethyl acetate (3×). The combined organic extracts were washed with saturated sodium bicarbonate solution and brine, filtered through a mixture of celite/silica gel. The filtrate was concentrated under reduced pressure providing crude (R)-2-((S)-3-benzyl-2-oxooxazolidin-4-yl)propanal (1.26 g) as a colorless oil, which was directly used without further purification. MS m/z 234.2 (M+H)+; Rt-0.60 min.

출처