Ethyl 4-thiomethylbenzoylformate → Hydroxy-(4-methylsulfanyl-phenyl)-acetic acid ethyl ester

HRID 857282Notes

Reaction equation

HRID 857282 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[C:5]([C:7]1[CH:12]=[CH:11][C:10]([S:13][CH3:14])=[CH:9][CH:8]=1)=[O:6])[CH3:2].[BH4-].[Na+]>CCO>[CH2:1]([O:3][C:4](=[O:15])[CH:5]([OH:6])[C:7]1[CH:12]=[CH:11][C:10]([S:13][CH3:14])=[CH:9][CH:8]=1)[CH3:2]

Participants

4

Reactant 2

HCID 2758911Ethyl 4-thiomethylbenzoylformateHCID 4311764Sodium borohydride

Product 1

HCID 20814961Hydroxy-(4-methylsulfanyl-phenyl)-acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (4-methylsulfanyl-phenyl)-oxo-acetic acid ethyl ester (Described in J. Med. Chem. 1981, 407) (1.0 eq) in EtOH (0.22M) at −78° C. was added NaBH4 (0.5 eq). The resulting mixture was stirred for 30 min then quenched at −78° C. by adding saturated aqueous NH4Cl. The residual mixture was concentrated, filtered on silica gel using EtOAc. The combined organic extracts were concentrated and the residual solid was recrystallised in Et2O/Hex to afford the desired compound as a yellow solid.

Workup

  1. customthen quenched at −78° C.
  2. additionby adding saturated aqueous NH4Cl
  3. concentrationThe residual mixture was concentrated
  4. filtrationfiltered on silica gel
  5. concentrationThe combined organic extracts were concentrated
  6. customthe residual solid was recrystallised in Et2O/Hex

Sources & evidence

ORD record
ord-a9eab7ec90584874afe41fcf7c0aabea
Source dataset
uspto-grants-2006_12
Patent number
US07144896B2

Reaction notes

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