Dimethyl Sulfoxide → (3aR,4R,5R,6aS)-hexahydro-2-oxo-5-(phenylmethoxy)-2H-cyclopenta[b]furan-4-carboxaldehyde
반응식
C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][CH2:12][C@@H:13]1[C@@H:20]2[C@@H:16]([O:17][C:18](=[O:21])[CH2:19]2)[CH2:15][C@H:14]1[O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(N(CC)CC)C>ClCCl>[O:21]=[C:18]1[O:17][C@H:16]2[CH2:15][C@@H:14]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C@H:13]([CH:12]=[O:11])[C@H:20]2[CH2:19]1참가 물질
반응물 4
생성물 1
시약·촉매·용매 1
실험 절차
To a solution of oxalyl chloride (3.3 mL, 38.1 mmoL) in dichloromethane (35 mL) at −78° C., was added DMSO (5.4 mL, 76.3 mmoL) and the mixture was stirred for 15 min. A solution of (3aR,4S,5R,6aS)-hexahydro-4-(hydroxymethyl)-5-(phenylmethoxy)-2H-cycloenta[b]furan-2-one (5, R1 is phenyl, and R2 and R3 are H, 5 g, 19 mmoL) in dichloromethane (35 mL) was then slowly added at −78° C. and the reaction mixture stirred for 0.5 h. Triethylamine (24 mL, 170 mmoL) was added at −78° C. and the reaction mixture stirred for 0.5 h. After completion of the reaction, the reaction mixture was washed with water (20 mL), and the organic layer was concentrated to dryness under vacuum to yield (3aR,4R,5R,6aS)-hexahydro-2-oxo-5-(phenylmethoxy)-2H-cyclopenta[b]furan-4-carboxaldehyde (6, R1 is phenyl, and R2 and R3 are H) in 80% yield.
후처리
- stirringthe reaction mixture stirred for 0.5 h
- stirringthe reaction mixture stirred for 0.5 h
- customAfter completion of the reaction
- washthe reaction mixture was washed with water (20 mL)
- concentrationthe organic layer was concentrated to dryness under vacuum
출처 및 근거
- ORD 기록
- ord-055dca477c4b4c599ef7edda83db796f
- 출처 데이터셋
- uspto-grants-2016_07
- 특허 번호
- US09382272B2
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