Tetrabutylammonium Fluoride → trans-7-cyano-5-(N-ethylsulfonyl-N-methylamino)-2,3,4,5-tetrahydro-1-benzoxepin-4-ol
Reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[O:19]1[CH:26]2[CH:20]1[CH2:21][CH2:22][O:23][C:24]1[CH:30]=[CH:29][C:28]([C:31]#[N:32])=[CH:27][C:25]=12.[CH3:33][N:34]([Si](C)(C)C)[S:35]([CH2:38][CH3:39])(=[O:37])=[O:36]>>[C:31]([C:28]1[CH:29]=[CH:30][C:24]2[O:23][CH2:22][CH2:21][C@@H:20]([OH:19])[C@H:26]([N:34]([S:35]([CH2:38][CH3:39])(=[O:37])=[O:36])[CH3:33])[C:25]=2[CH:27]=1)#[N:32]Participants
4
Conditions
- Temperature
- 60 °C
Procedure
1.5 g of tetrabutylammonium fluoride were added with stirring to a mixture of 4 g of 4,5-epoxy-2,3,4,5-tetrahydro-1-benzoxepine-7-carbonitrile (J. Chem. Soc., Perkin Trans. 1 (1991), 2763) and 7.0 g of N-methyl-N-trimethylsilylethanesulfonamide. The reaction mixture was then heated for 3 h at 60° C., stirred overnight at RT and poured onto ammonium chloride solution. It was extracted several times with EA, and the organic phase was washed with water and dried over sodium sulfate. After concentration and recrystallization of the solid residue from cyclohexane/EA (1:5), 3.2 g of trans-7-cyano-5-(N-ethylsulfonyl-N-methylamino)-2,3,4,5-tetrahydro-1-benzoxepin-4-ol were obtained, m.p. 142-144° C.
Workup
- additionpoured onto ammonium chloride solution
- extractionIt was extracted several times with EA
- washthe organic phase was washed with water
- dry with materialdried over sodium sulfate
- concentrationAfter concentration and recrystallization of the solid residue from cyclohexane/EA (1:5)
Sources & evidence
- ORD record
- ord-0bd1291bc45e4dbd8e0803e84d6aab29
- Source dataset
- uspto-grants-2001_12
- Patent number
- US06333349B1
Reaction notes
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