Tetrabutylammonium Fluoride Trihydrate → 7-Nitro-trans-5-(5-chloro-1,2-dihydro-2-oxo-pyrid-1-yl)-2,3,4,5-tetrahydro-1-benzoxepin-4-ol
Reaction equation
[OH2:1].O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[O:22]1[CH:29]2[CH:23]1[CH2:24][CH2:25][O:26][C:27]1[CH:33]=[CH:32][C:31]([N+:34]([O-:36])=[O:35])=[CH:30][C:28]=12.[Cl:37][C:38]1[CH:39]=[CH:40][C:41]([Si](C)(C)C)=[N:42][CH:43]=1>>[N+:34]([C:31]1[CH:32]=[CH:33][C:27]2[O:26][CH2:25][CH2:24][C@@H:23]([OH:22])[C@H:29]([N:42]3[CH:43]=[C:38]([Cl:37])[CH:39]=[CH:40][C:41]3=[O:1])[C:28]=2[CH:30]=1)([O-:36])=[O:35]Participants
4
Conditions
- Temperature
- 60 °C
Procedure
6.63 g (21 mmol) of tetrabutylammonium fluoride trihydrate are added to a stirred mixture of 3.93 g (19 mmol) of 4,5-epoxy-7-nitro-2,3,4,5-tetrahydro-1-benzoxepin and 8.06 g (40 mmol) of 5-chloro-2-trimethylsilyl-pyridine, and the mixture is heated at 60° C. for 5 hours. The mixture is then stirred into ice-water and extracted several times with ethyl acetate. The combined ethyl acetate extracts are washed with water and saturated sodium chloride solution dried over sodium sulfate, filtered and evaporated in vacuo. The remaining viscous oil crystallizes after standing for some time. It is triturated with ethyl acetate and filtered off with suction. Crystals of melting point 219°-222° C. are obtained.
Workup
- extractionextracted several times with ethyl acetate
- washThe combined ethyl acetate extracts are washed with water and saturated sodium chloride solution
- dry with materialdried over sodium sulfate
- filtrationfiltered
- customevaporated in vacuo
- customThe remaining viscous oil crystallizes
- customIt is triturated with ethyl acetate
- filtrationfiltered off with suction
- customCrystals of melting point 219°-222° C. are obtained
Sources & evidence
- ORD record
- ord-ec2cea65ada8406289989e264b095ac0
- Source dataset
- uspto-grants-1993_03
- Patent number
- US05194442
Reaction notes
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