Dimethyl Sulfoxide → (3aR,4R,5R,6aS)-hexahydro-2-oxo-5-(phenylmethoxy)-2H-cyclopenta[b]furan-4-carboxaldehyde
Reaction equation
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]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
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.
Workup
- 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
Sources & evidence
- ORD record
- ord-055dca477c4b4c599ef7edda83db796f
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09382272B2
Reaction notes
Loading…