Potassium peroxymonosulphate → Ethyl 2,3-dihydro-9-methanesulfinyl-1-benzoxepin-4-carboxylate

HRID 1699396Notes

Reaction equation

HRID 1699396 reaction equation
S([O-])(O[O-])(=O)=[O:2].[K+].[K+].[CH3:9][S:10][C:11]1[C:21]2[O:20][CH2:19][CH2:18][C:17]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:16][C:15]=2[CH:14]=[CH:13][CH:12]=1>O.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>[CH3:9][S:10]([C:11]1[C:21]2[O:20][CH2:19][CH2:18][C:17]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:16][C:15]=2[CH:14]=[CH:13][CH:12]=1)=[O:2]

Participants

6

Reactant 2

HCID 10313463Potassium peroxymonosulphateHCID 18319598HCID 18319598, compound

Product 1

HCID 18319611Ethyl 2,3-dihydro-9-methanesulfinyl-1-benzoxepin-4-carboxylateYield 23.6%

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of potassium peroxymonosulfate (6.7 g) in water (33 ml) was added dropwise to a mixture of ethyl 2,3-dihydro-9-methylthio-1-benzoxepin-4-carboxylate (2.6 g) and tetrabutylammonium hydrogen sulfate (0.7 g) in ethyl acetate (26 ml) and water (13 ml) and the mixture was stirred at ambient temperature for 2.5 hours. The separated organic layer was washed with 10% aqueous sodium thiosulfate. The organic layer was washed with water, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel using a mixture of ethyl acetate and toluene (1:1) as an eluent. The eluted fractions containing the desired product were collected and evaporated in vacuo to give ethyl 2,3-dihydro-9-methanesulfinyl-1-benzoxepin-4-carboxylate (0.65 g).

Workup

  1. washThe separated organic layer was washed with 10% aqueous sodium thiosulfate
  2. washThe organic layer was washed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by column chromatography on silica gel using
  6. additiona mixture of ethyl acetate and toluene (1:1) as an eluent
  7. additionThe eluted fractions containing the desired product
  8. customwere collected
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-81546b850f244f69bc3ef7a68c55ce54
Source dataset
uspto-grants-2002_02
Patent number
US06346527B1

Reaction notes

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