Methanol → HCID 67301623, compound

HRID 643618Notes

Reaction equation

HRID 643618 reaction equation
O=S(Cl)Cl.[Cl:5][C:6]1[CH:7]=[C:8]([CH2:13][C@@H:14]([OH:18])[C:15]([OH:17])=[O:16])[CH:9]=[CH:10][C:11]=1[CH3:12].[CH3:19]O>>[Cl:5][C:6]1[CH:7]=[C:8]([CH2:13][C@@H:14]([OH:18])[C:15]([O:17][CH3:19])=[O:16])[CH:9]=[CH:10][C:11]=1[CH3:12]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 67301744HCID 67301744, compound

Product 1

HCID 67301623HCID 67301623, compound

Conditions

Temperature
0 °C

Procedure

2.0 mL (27.4 mmol) SOCl2 were slowly added dropwise to a solution of 2.8 g (10.4 mmol) of (R)-3-(3-chloro-4-methyl-phenyl)-2-hydroxy-propionic acid in 100 mL MeOH while cooling with ice and the reaction solution was stirred for 1 h at 0° C. and for 1 h at RT. The reaction mixture was evaporated down i.vac., the residue was taken up in EtOAc, the organic phase was washed with saturated NaHCO3 solution and dried over Na2SO4. After the desiccant and solvent had been eliminated the residue was purified by chromatography (silica gel, gradient DCM to DCM/MeOH 50:1).

Workup

  1. temperaturewhile cooling with ice
  2. customThe reaction mixture was evaporated down i.vac
  3. washthe organic phase was washed with saturated NaHCO3 solution
  4. dry with materialdried over Na2SO4
  5. customwas purified by chromatography (silica gel, gradient DCM to DCM/MeOH 50:1)

Sources & evidence

ORD record
ord-8dfb9014ac6e4ed7bb8f26119659cc9c
Source dataset
uspto-grants-2010_04
Patent number
US07700598B2

Reaction notes

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