Water → HCID 59457683, compound

HRID 1711093Notes

Reaction equation

HRID 1711093 reaction equation
[F:1][C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][C:11]([O:13]C)=[O:12])=[CH2:3].[Li+].[OH-].O>O.C1COCC1>[F:1][C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][C:11]([OH:13])=[O:12])=[CH2:3]

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 59457664HCID 59457664, compound

Product 1

HCID 59457683HCID 59457683, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

A suspension of methyl 2-(2-(1-fluorovinyl)phenyl)acetate (334, 770.8 mg, 4.015 mmol) (Hakamoto T.; Kobavashi T. J. Org. Chem. 2003, 68, 6354-6359) and LiOH×H2O (185 mg, 4.41 mmol) in H2O/THF (1:1, 11 mL) was stirred overnight at room temperature. The THF was evaporated off under reduced pressure; the aqueous residue was diluted with water, washed with EtOAc, acidified to pH˜3 by addition of 1N HCl and extracted with DCM. The organic extract was dried over anhydrous Na2SO4 and concentrated under reduced pressure affording 335 (557.2 mg, 77% yield) as a white solid. LCMS: (M−1) 187.1 (100%).

Workup

  1. customThe THF was evaporated off under reduced pressure
  2. additionthe aqueous residue was diluted with water
  3. washwashed with EtOAc
  4. additionacidified to pH˜3 by addition of 1N HCl
  5. extractionextracted with DCM
  6. extractionThe organic extract
  7. dry with materialwas dried over anhydrous Na2SO4
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-01c79a2451ce492f9b3bc5292d65dec2
Source dataset
uspto-grants-2010_09
Patent number
US07790729B2

Reaction notes

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