Dimethyl Sulfide → Ethylsulfanyl-3-(4-hydroxyphenyl)propanoic acid methyl ester

HRID 987281Notes

Reaction equation

HRID 987281 reaction equation
[CH3:1][O:2][C:3](=[O:23])[CH:4]([S:20][CH2:21][CH3:22])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12]CC2C=CC=CC=2)=[CH:8][CH:7]=1.CSC.B(F)(F)F.CCOCC>ClCCl>[CH3:1][O:2][C:3](=[O:23])[CH:4]([S:20][CH2:21][CH3:22])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 1068Dimethyl SulfideHCID 8000Boron trifluoride etherateHCID 541051323-(4-Benzyloxyphenyl)-2-ethylsulfanyl propanoic acid methyl ester

Product 1

HCID 54450181Ethylsulfanyl-3-(4-hydroxyphenyl)propanoic acid methyl esterYield 74.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(4-Benzyloxyphenyl)-2-ethylsulfanyl propanoic acid methyl ester (0,37 g; 1.12 mmole) was dissolved in dichloromethane (3.5 ml). Dimethylsulfide (3 ml), was added followed by addition of boron trifluoride etherate (1.6 g; 11 mmole), The reaction mixture was stirred for 3 hours at room temperature and then quenched with water (3 ml). More dichloromethane was added and the phases were separated. The organic phase was washed twice with brine and dried with sodium sulfate. Evaporation of the solvent gave 0.2 g (74.3% yield) of ethylsulfanyl-3-(4-hydroxyphenyl)propanoic acid methyl ester.

Workup

  1. customquenched with water (3 ml)
  2. additionMore dichloromethane was added
  3. customthe phases were separated
  4. washThe organic phase was washed twice with brine
  5. dry with materialdried with sodium sulfate
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-f3697aba57014f12964ca3ec80d564e3
Source dataset
uspto-grants-2003_10
Patent number
US06630600B1

Reaction notes

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