Dichloromethane → N-{2-(6-oxabicyclo[3.1.0]hex-2-yloxy)phenyl}acetamide

HRID 496188Notes

Reaction equation

HRID 496188 reaction equation
[CH:1]1([O:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[NH:13][C:14](=[O:16])[CH3:15])[CH2:5][CH2:4][CH:3]=[CH:2]1.ClCCl.C([O:24]C)(C)(C)C>>[CH:2]12[O:24][CH:3]1[CH2:4][CH2:5][CH:1]2[O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[NH:13][C:14](=[O:16])[CH3:15]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 15413tert-Butyl methyl etherHCID 22313646N-[2-(2-cyclopenten-1-yloxy)phenyl]acetamide

Product 1

HCID 22313665N-{2-(6-oxabicyclo[3.1.0]hex-2-yloxy)phenyl}acetamideYield 58%

Procedure

To an ice bath cooled solution of N-[2-(2-cyclopenten-1-yloxy)phenyl]acetamide (149 mg, 686 μmol, 1.0 equiv.) in dichloromethane (4 ml) m-chloroperbenzoic acid (85 proc.; 146 μmol, 1.1 equiv.) was added. After stirring overnight with slowly warming up to an ambient temperature the reaction mixture was diluted by tertbutyl(methyl)ether, washed successively by a sat. sodium bisulfate solution, 5 proc. sodium hydroxide and brine and dried over sodium sulfate. Evaporation of the solvent and flash chromatography on silica gel (ethyl acetate/heptane, 2:3 continued to ethyl acetate) yielded 93 mg (58%) of the subtitle compound as a mixture of the trans, (minor) and the cis (major) diastereoisomeric epoxides as a pale yellow oil. The cis/trans ratio was determined as 2:1 by 1H-NMR.

Workup

  1. additionwas added
  2. washwashed successively by a sat. sodium bisulfate solution, 5 proc
  3. dry with materialsodium hydroxide and brine and dried over sodium sulfate
  4. customEvaporation of the solvent and flash chromatography on silica gel (ethyl acetate/heptane, 2:3 continued to ethyl acetate)

Sources & evidence

ORD record
ord-7f8990b169f9448d88c7626baeeb80a9
Source dataset
uspto-grants-2005_09
Patent number
US06943188B2

Reaction notes

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