Sodium Hydroxide → HCID 22261597, compound

HRID 1610718Notes

Reaction equation

HRID 1610718 reaction equation
[C:1]([C:5]1[CH:26]=[CH:25][C:8]([CH2:9][CH:10]([C:16]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)=[O:17])[C:11]([O:13]CC)=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>O1CCCC1CO>[C:1]([C:5]1[CH:26]=[CH:25][C:8]([CH2:9][CH:10]([CH:16]([C:18]2[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=2)[OH:17])[C:11]([OH:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22261735HCID 22261735, compound

Product 1

HCID 22261597HCID 22261597, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 7360Tetrahydrofurfuryl alcoholSolvent

Procedure

To a solution of ethyl 2-[4-(tert-butyl)benzyl]-3-(4-fluorophenyl)-3-oxopropionate (7.43 g, 20.7 mmol) in tetrahydrofuran-methanol (20 ml-20 ml) was added sodium hydroxide at room temperature, and the mixture was stirred overnight at room temperature. After completion of the reaction, the organic solvent was evaporated under reduced pressure, and the residue was acidified with 1N hydrochloric acid and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. Recrystallization from hexane-ethyl acetate gave (2RS,3RS)-2-[4-(tert-butyl)benzyl]-3-(4-fluorophenyl)-3-hydroxypropionic acid (5.51 g, 81%) as colorless crystals.

Workup

  1. customAfter completion of the reaction
  2. customthe organic solvent was evaporated under reduced pressure
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customRecrystallization from hexane-ethyl acetate

Sources & evidence

ORD record
ord-53d09315816c4aff9e2730c24871dc68
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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