Water → HCID 12926046, compound

HRID 894636Notes

Reaction equation

HRID 894636 reaction equation
[CH3:1][S:2][C:3]1[CH:14]=[CH:13][C:6]2[O:7][C:8]3([C:11](=[O:12])[C:5]=2[CH:4]=1)[CH2:10][CH2:9]3.ClC1C=CC=C(C(OO)=[O:23])C=1.[OH2:26]>ClCCl>[CH3:1][S:2]([C:3]1[CH:14]=[CH:13][C:6]2[O:7][C:8]3([C:11](=[O:12])[C:5]=2[CH:4]=1)[CH2:10][CH2:9]3)(=[O:23])=[O:26]

Participants

5

Reactant 3

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 12926045HCID 12926045, compound

Product 1

HCID 12926046HCID 12926046, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-methylthiospiro[benzo[b]furan-2(3H), 1'-cyclopropane]-3-one (103.1 mg.) in dichloromethane (2.1 ml.) was added in small portions of m-chloroperbenzoic acid (215.7 mg.) under stirring. After stirring for one hour, the reaction mixture was diluted with water and extracted with chloroform. The extract was washed with aqueous solution of sodium hydrogen carbonate, aqueous solution of sodium hydrosulfite and water in that order, and after drying the solvent was removed by evaporation under reduced pressure. The residue was recrystallized from ethanol-water to give colorless needles of 5-methylsulfonylspiro[benzo[b]furan-2(3H), 1'-cyclopropane]-3-one (85 mg.). This product was identical with the compound of Example 64 in melting point and spectral data.

Workup

  1. stirringAfter stirring for one hour
  2. extractionextracted with chloroform
  3. washThe extract was washed with aqueous solution of sodium hydrogen carbonate, aqueous solution of sodium hydrosulfite and water in that order
  4. customafter drying the solvent
  5. customwas removed by evaporation under reduced pressure
  6. customThe residue was recrystallized from ethanol-water

Sources & evidence

ORD record
ord-49ce82f080b048079bfa971cf2d6f5be
Source dataset
uspto-grants-1981_08
Patent number
US04284644

Reaction notes

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