Methanol → HCID 59455495, compound

HRID 1909595Notes

Reaction equation

HRID 1909595 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([F:15])=[CH:13][C:12]([CH2:16][CH:17]([CH3:21])[C:18]([O-:20])=[O:19])=[CH:11][C:10]=1[F:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.[OH-].[Li+]>O1CCCC1.O>[CH2:1]([O:8][C:9]1[C:10]([F:22])=[CH:11][C:12]([CH2:16][CH:17]([CH3:21])[C:18]([OH:20])=[O:19])=[CH:13][C:14]=1[F:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 86643716HCID 86643716, compound

Product 1

HCID 59455495HCID 59455495, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 3-(4-(benzyloxy)-3,5-difluorophenyl)-2-methylpropanoate (752) (1.09 g, 3.26 mmol) in tetrahydrofuran (10 mL), water (10 mL), and methanol (20 mL) was added lithium hydroxide (547 mg, 13.04 mmol) and the solution was stirred overnight at 80° C. The reaction was concentrated, acidified with 1N hydrochloric acid, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo to yield 3-(4-(benzyloxy)-3,5-difluorophenyl)-2-methylpropanoic acid (753).

Workup

  1. concentrationThe reaction was concentrated
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-03f26a14fb23414ab0ff16f251798aa2
Source dataset
uspto-grants-2013_12
Patent number
US08598374B2

Reaction notes

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