Benzoyl chloride → Benzyl 9-benzoyl-1,2,3,4-tetrahydrocarbazole-3-carboxylate
Reaction equation
[H-].[Na+].[C:3](Cl)(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Cl-].[NH4+:13]>CN(C)C=O>[C:3]([N:13]1[C:7]2[CH2:8][CH2:9][CH:4]([C:3]([O:10][CH2:3][C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=3)=[O:10])[CH2:5][C:6]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 291 mg of benzyl 1,2,3,4-tetrahydrocarbazole-3-carboxylate, as obtained in Example 50, in 2 ml of N,N-dimethylformamide was added, with ice-cooling, to a suspension of 87 mg of sodium hydride (55% w/w dispersion in mineral oil) in 4 ml of N,N-dimethylformamide. 0.12 ml of benzoyl chloride was added to the reaction mixture which was then stirred for 1 hour. After this time, a saturated aqueous solution of ammonium chloride was added to the reaction mixture. The aqueous layer was extracted with ethyl acetate, and the organic extract was washed with water, dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure. The resulting residue was subjected to column chromatography using 10 g of silica gel with a 5:1 v/v mixture of hexane and ethyl acetate as the eluent, to yield 384 mg of the title compound as an oil.
Workup
- additionwas added, with ice-
- extractionThe aqueous layer was extracted with ethyl acetate
- extractionthe organic extract
- washwas washed with water
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated by evaporation under reduced pressure
- additionwith a 5:1 v/v mixture of hexane and ethyl acetate as the eluent
Sources & evidence
- ORD record
- ord-1fd870dffa0b4777ada4ec21ff2ce7f4
- Source dataset
- uspto-grants-1999_03
- Patent number
- US05877199
Reaction notes
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