Dimethyl Sulfide → (2S)-3-(2-chloro-4-hydroxy-phenyl)-2-ethoxy-propionic acid methyl ester

HRID 1064936Notes

Reaction equation

HRID 1064936 reaction equation
CSC.B(F)(F)F.CCOCC.[CH3:13][O:14][C:15](=[O:36])[C@@H:16]([O:33][CH2:34][CH3:35])[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24]CC2C=CC=CC=2)=[CH:20][C:19]=1[Cl:32]>ClCCl>[CH3:13][O:14][C:15](=[O:36])[C@@H:16]([O:33][CH2:34][CH3:35])[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][C:19]=1[Cl:32]

Participants

5

Reactant 3

HCID 1068Dimethyl SulfideHCID 8000Boron trifluoride etherateHCID 68616300(2S)-3-(4-benzyloxy-2-chloro-phenyl)-2-ethoxy-propionic acid methyl ester

Product 1

HCID 68616433(2S)-3-(2-chloro-4-hydroxy-phenyl)-2-ethoxy-propionic acid methyl esterYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dimethyl sulfide (5.8 ml, 79 mmol) and boron trifluoride diethyl etherate (46% purity, 4.3 ml, 16 mmol) were added to a ice cold solution of (2S)-3-(4-benzyloxy-2-chloro-phenyl)-2-ethoxy-propionic acid methyl ester (1.1 g, 3.2 mmol) in dichloromethane (34 ml) under an argon atmosphere. The mixture was stirred for 5 h at ambient temperature, poured into ice water/brine 1/1 and extracted two times with dichloromethane. The combined extracts were washed with ice water/brine 1/1 and dried over sodium sulfate. Removal of the solvent under reduced pressure gave a colorless oil which was purified by column chromatography (silica gel, cyclohexane/AcOEt) to yield 0.6 g (2.3 mmol, 74%) of the title compound as colorless oil.

Workup

  1. extractionextracted two times with dichloromethane
  2. washThe combined extracts were washed with ice water/brine 1/1
  3. dry with materialdried over sodium sulfate
  4. customRemoval of the solvent under reduced pressure
  5. customgave a colorless oil which
  6. customwas purified by column chromatography (silica gel, cyclohexane/AcOEt)

Sources & evidence

ORD record
ord-48eed2ae151d4129b1975df51476de91
Source dataset
uspto-grants-2005_11
Patent number
US06969725B2

Reaction notes

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