Potassium Carbonate → 1-(5-benzenesulfonyl-2-(S)-oxiranylmethoxy-phenyl)-ethanone

HRID 2221301Notes

Reaction equation

HRID 2221301 reaction equation
[CH2:1]([C@@H:3]1[O:5][CH2:4]1)Cl.[C:6]1([S:12]([C:15]2[CH:16]=[CH:17][C:18]([OH:24])=[C:19]([C:21](=[O:23])[CH3:22])[CH:20]=2)(=[O:14])=[O:13])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.C(OCC)(=O)C>[C:6]1([S:12]([C:15]2[CH:16]=[CH:17][C:18]([O:24][CH2:1][C@@H:3]3[CH2:4][O:5]3)=[C:19]([C:21](=[O:23])[CH3:22])[CH:20]=2)(=[O:14])=[O:13])[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2734062(-)-EpichlorohydrinHCID 189877381-(5-Benzenesulfonyl-2-hydroxy-phenyl)-ethanone

Product 1

HCID 866015571-(5-benzenesulfonyl-2-(S)-oxiranylmethoxy-phenyl)-ethanone

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

(R)-(−)Epichlorhydrin (1.93 g; 0.021 mol) was added to a suspension of 1-(5-benzenesulfonyl-2-hydroxy-phenyl)-ethanone (1.92 g; 0.007 mol) and potassium carbonate (1.44 g; 0.011 mol) in acetonitrile (5 mL). The mixture was heated under reflux for 18 hours. After cooling to ambient temperature, the mixture was diluted with ethyl acetate, filtered, washed with water and saturated sodium bicarbonate, dried (Na2SO4) and concentrated in vacuo. The crude material was purified by flash chromatography on silica gel (hexane-ethyl acetate; 7:3) to give 1-(5-benzene sulfonyl-2-(S)-oxiranylmethoxy-phenyl)-ethanone as a white solid (1.456 g; 63%). A sample was recrystallized from diethyl ether-hexane: M. p. 115.1-116.8° C. Similarly, but replacing (R)-(−)epichlorhydrin with (S)-(+)epichlorhydrin, 1-(5-benzene sulfonyl-2-(R)-oxiranylmethoxy-phenyl)-ethanone was prepared. M. p. 111.9-113.5° C. Similarly, but replacing 1-(5-benzenesulfonyl-2-hydroxy-phenyl)-ethanone with 1-[5-(3-fluoro-benzenesulfonyl)-2-hydroxy-phenyl]-ethanone, the above procedure gave 1-[5-(3-fluoro-benzenesulfonyl)-2-(S)-oxiranylmethoxy-phenyl]-ethanone: M. p. 112.7-114.9° C. Replacing 1-(5-benzenesulfonyl-2-hydroxy-phenyl)-ethanone with 1-[5-(3-Fluoro-benzenesulfonyl)-2-hydroxy-phenyl]-ethanone and replacing (R)-(−)epichlorhydrin with (S)-(+)epichlorhydrin gave 1-[5-(3-Fluoro-benzenesulfonyl)-2-(R)-oxiranylmethoxy-phenyl]-ethanone. M. p. 118.3-120.5° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 18 hours
  3. filtrationfiltered
  4. washwashed with water and saturated sodium bicarbonate
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe crude material was purified by flash chromatography on silica gel (hexane-ethyl acetate; 7:3)

Sources & evidence

ORD record
ord-54ceaf446b4a49ef9ccd615e22eabadc
Source dataset
uspto-grants-2008_05
Patent number
US07368567B2

Reaction notes

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