Benzoyl chloride → HCID 14347867, compound
Reaction equation
[CH3:1][C@H:2]([CH2:7][S:8][CH3:9])[C@@H:3]([OH:6])[CH2:4][OH:5].[C:10](Cl)(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>N1C=CC=CC=1.CCOCC>[C:10]([O:5][CH2:4][C@H:3]([OH:6])[C@@H:2]([CH3:1])[CH2:7][S:8][CH3:9])(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
To a stirred, ice-cooled solution of (B) (3.7g.,0.025m.) in dried pyridine (30 ml.) was added dropwise over ca. 5 minutes under a nitrogen atmosphere a solution of benzoyl chloride (3.0 ml., 0.026m.) in dry ether (5 ml.). The mixture was stirred for an additional 5 minutes, the ice-bath removed, and the mixture allowed to stir at ambient temperatures. After ca.1.5 hr., tlc analysis indicated that the reaction was complete and the mixture was transferred to a separatory funnel with ether (300 ml.). The mixture was washed IX with water (100 ml.), 4 X with saturated copper sulfate solution, lX with saturated sodium chloride solution and dried over sodium sulfate. Concentration of the filtered solution followed by chromatography on silica gel (200g.; 1% methanol/methylene chloride as eluant) yielded 5.4g (C) as an oil. N.m.r. was consistent with the structure [α]D =30 9.1 (c=0.75, CDCl3).
Workup
- customthe ice-bath removed
- stirringto stir at ambient temperatures
- custom1.5 hr
- customthe mixture was transferred to a separatory funnel with ether (300 ml.)
- washThe mixture was washed IX with water (100 ml.), 4 X with saturated copper sulfate solution, lX with saturated sodium chloride solution
- dry with materialdried over sodium sulfate
Sources & evidence
- ORD record
- ord-8d563786cb114b669f250fa41325cc56
- Source dataset
- uspto-grants-1989_12
- Patent number
- US04885276
Reaction notes
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