m-Chloroperbenzoic acid → (+/-)-7-(2'-Acetoxyethyl)-2-oxepanone
Reaction equation
C(=O)(O)[O-].[Na+].[CH:6]1[CH:11]=[C:10](Cl)[CH:9]=[C:8]([C:13]([O:15]O)=[O:14])[CH:7]=1.[C:17]([O:20][CH2:21]CC1CCCCC1=O)(=[O:19])[CH3:18]>ClCCl>[C:17]([O:20][CH2:21][CH2:9][CH:10]1[O:15][C:13](=[O:14])[CH2:8][CH2:7][CH2:6][CH2:11]1)(=[O:19])[CH3:18]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Under an argon atmosphere, sodium bicarbonate (1.78 g, 21.20 mmol) and 80-90% w/w MCPBA (4.95 g, 28.26 mmol) were added to a solution of (±)-2-(2'-acetoxyethyl)cyclohexanone (2.60 g, 14.13 mmol) (0.50 mmol) in dichloromethane (70 ml) at room temperature. The mixture was stirred at room temperature for 3 h, and diluted with dichloromethane (80 ml) and washed sequentially with a saturated sodium sulphite solution (3×100 ml), distilled water (100 ml) and brine (100 ml). The organic phase was dried over magnesium sulphate. After filtration, the solvent was evaporated under reduced pressure to give the crude product which was purified by flash column chromatography using hexane-ethyl acetate (2:3) as eluent to give (±)-7-(2'-acetoxyethyl)-2-oxepanone, as a colourless oil (2.76 g, 98% yield). Rf 0.40 (hexane-ethyl acetate, 7:3).
Workup
- washwashed sequentially with a saturated sodium sulphite solution (3×100 ml)
- distillationdistilled water (100 ml) and brine (100 ml)
- dry with materialThe organic phase was dried over magnesium sulphate
- filtrationAfter filtration
- customthe solvent was evaporated under reduced pressure
- customto give the crude product which
- customwas purified by flash column chromatography
Sources & evidence
- ORD record
- ord-a22791c55d7144289f59ea0e3740ed9c
- Source dataset
- uspto-grants-2000_10
- Patent number
- US06140512
Reaction notes
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