Water → 5-Chloro-2-(4-fluorophenyl)-2-methoxyvaleric acid

HRID 1009401Notes

Reaction equation

HRID 1009401 reaction equation
[OH-].[Na+].[Cl:3][CH2:4][CH2:5][CH2:6][C:7]([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)([O:12][CH3:13])[C:8]([O:10]C)=[O:9].O>C1COCC1.CO>[Cl:3][CH2:4][CH2:5][CH2:6][C:7]([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)([O:12][CH3:13])[C:8]([OH:10])=[O:9]

Participants

6

Procedure

A 4 N sodium hydroxide solution (0.2 mL) was added to a mixed solution of methyl 5-chloro-2-(4-fluorophenyl)-2-methoxyvalerate (141 mg) in THF (1 mL) and methanol (0.5 mL), and the reaction solution was stirred at room temperature for 3.5 hours. Methanol (0.5 mL) and a 4 N sodium hydroxide solution (0.1 mL) were added to the reaction solution, and the reaction solution was further stirred at room temperature for 1.5 hours. Water was added to the reaction solution which was then washed with diethyl ether. 1 N hydrochloric acid (1.4 mL) and ethyl acetate were added to the resulting aqueous layer, and the organic layer was separated. The resulting ethyl acetate layer was washed with brine and dried over anhydrous magnesium sulfate. The resulting ethyl acetate layer was concentrated under reduced pressure to obtain 109 mg of the title compound. The property values of the compound are as follows.

Workup

  1. stirringthe reaction solution was further stirred at room temperature for 1.5 hours
  2. washwas then washed with diethyl ether
  3. addition1 N hydrochloric acid (1.4 mL) and ethyl acetate were added to the resulting aqueous layer
  4. customthe organic layer was separated
  5. washThe resulting ethyl acetate layer was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationThe resulting ethyl acetate layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7737f7c569a744fa9154a4b1e1447cc4
Source dataset
uspto-grants-2011_07
Patent number
US07973033B2

Reaction notes

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