Pyridine → 3-Propyloxetan-3-ylmethyl 4-(2,2-dibromovinyl)cyclohexanecarboxylate
Reaction equation
[Br:1][C:2]([Br:13])=[CH:3][CH:4]1[CH2:9][CH2:8][CH:7]([C:10](Cl)=[O:11])[CH2:6][CH2:5]1.[CH2:14]([C:17]1([CH2:21][OH:22])[CH2:20][O:19][CH2:18]1)[CH2:15][CH3:16].N1C=CC=CC=1>ClCCl>[Br:1][C:2]([Br:13])=[CH:3][CH:4]1[CH2:9][CH2:8][CH:7]([C:10]([O:22][CH2:21][C:17]2([CH2:14][CH2:15][CH3:16])[CH2:20][O:19][CH2:18]2)=[O:11])[CH2:6][CH2:5]1Participants
Procedure
4-(2,2-Dibromovinyl)cyclohexanecarbonyl chloride (0.91 g) in dry dichloromethane (5 ml) was added to a cooled (0° C.) solution of 3-propyl-3-hydroxymethyloxetane (0.406 g) and pyridine (0.64 ml) in dry dichloromethane (10 ml) under a stream of nitrogen. The reaction mixture was allowed to warm to room temperature and to stir overnight. Further dichloromethane was added. The organic phase was then washed with dilute hydrochloric acid, saturated sodium bicarbonate solution and brine before drying over anhydrous magnesium sulphate. The solvent was evaporated in vacuo and the residue was purified by column chromatography on silica gel, pre-eluted with hexane containing 1% triethylamine. Elution with hexane/ether (3:1) gave 3-propyloxetan-3-ylmethyl 4-(2,2-dibromovinyl)cyclohexanecarboxylate (0.6 g) as a mixture of cis- and trans-isomers.
Workup
- washThe organic phase was then washed with dilute hydrochloric acid, saturated sodium bicarbonate solution and brine
- dry with materialbefore drying over anhydrous magnesium sulphate
- customThe solvent was evaporated in vacuo
- customthe residue was purified by column chromatography on silica gel
- washpre-eluted with hexane containing 1% triethylamine
- washElution with hexane/ether (3:1)
Sources & evidence
- ORD record
- ord-b29445106cdf4f4fb6c85c1dd75ef2c3
- Source dataset
- uspto-grants-1992_05
- Patent number
- US05116862
Reaction notes
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