Nitroethane → (3aS,6aS)-rel-3-methyl-3a,4,6,6a-tetrahydrofuro[3,4-d]isoxazole
Reaction equation
[O:1]1[CH2:5][CH:4]=[CH:3][CH2:2]1.[N+:6]([CH2:9][CH3:10])([O-])=[O:7].C(N(CC)CC)C.C1(N=C=O)C=CC=CC=1>CCOCC>[CH3:10][C:9]1[C@H:3]2[CH2:2][O:1][CH2:5][C@H:4]2[O:7][N:6]=1Participants
6
Procedure
A solution of 2,5-dihydrofuran (5 g, 69.9 mmol) in ether (90 ml) was treated dropwise with a solution of nitroethane (5.46 g, 71.3 mmol) in ether (15 ml) at room temperature. Thereafter, triethylamine (70.7 mg, 699 μmol) was added followed by the dropwise addition of phenyl isocyanate (17.3 g, 143 mmol). The reaction mixture was stirred for 3 days at room temperature. For the workup, the white precipitate was filtered and washed with ether. The filtrate was evaporated and the crude product was purified by chromatography using a gradient of heptane and ethyl acetate=100:0 to 50:50 as the eluent. After a second chromatography the (3aS,6aS)-rel-3-methyl-3a,4,6,6a-tetrahydrofuro[3,4-d]isoxazole (58% yield) was obtained as a yellow oil.
Workup
- filtrationFor the workup, the white precipitate was filtered
- washwashed with ether
- customThe filtrate was evaporated
- customthe crude product was purified by chromatography
Sources & evidence
- ORD record
- ord-3bd4c813f2f24839bd991aaafafc5a66
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09067924B2
Reaction notes
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