Triethyl phosphite → 7,8-dihydro-6,6-dimethyl-7,8-epoxy-6H-pyrano[2,3-f]benz-2,1,3-oxadiazole
Reaction equation
[CH3:1][C:2]1([CH3:17])[O:15][C:6]2=[CH:7][C:8]3[C:9]([CH:14]=[C:5]2[CH:4]2[O:16][CH:3]12)=[N:10][O:11][N+:12]=3[O-].P(OCC)(OCC)OCC>C1C=CC=CC=1>[CH3:1][C:2]1([CH3:17])[O:15][C:6]2=[CH:7][C:8]3[C:9]([CH:14]=[C:5]2[CH:4]2[O:16][CH:3]12)=[N:10][O:11][N:12]=3Participants
4
Procedure
To a mixture of 1.00 g (4.27 m mol) of 7,8-dihydro-6,6-dimethyl-7,8-epoxy-6H-pyrano [2,3-f] benzo-2,1,3-oxadiazole 3-oxide and 6 ml of benzene was added dropwise 0.80 ml (4.70 m mol) of triethyl phosphite over 15 minutes at 60° C. under stirring. Then, the mixture was stirred for three hours. After the solvent was removed under the reduced pressure, the residue was subjected to a silica gel column chromatography using a developing solvent of ethyl acetate-hexane (1:1 (v/v)) to obtain 0.82 g of the intended compound (yield: 88%). A part of the obtained compound was recrystallized from hexane to obtain yellow crystals (m.p.: 97° to 99° C.).
Workup
- stirringThen, the mixture was stirred for three hours
- customAfter the solvent was removed under the reduced pressure
Sources & evidence
- ORD record
- ord-1ee5f32bfddb4d9a965f576aa831e8e3
- Source dataset
- uspto-grants-1990_02
- Patent number
- US04900752
Reaction notes
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