Lithium Hydroxide → HCID 59130999, compound

HRID 1992680Notes

Reaction equation

HRID 1992680 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1/[CH:9]=[CH:10]\[C:11]([O:13]C)=[O:12].[OH-].[Li+]>O1CCCC1>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1/[CH:9]=[CH:10]\[C:11]([OH:13])=[O:12]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 59130984HCID 59130984, compound

Product 1

HCID 59130999HCID 59130999, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl (2Z)-3-(2,4-difluorophenyl)acrylate, from preparation 34 (1.3 g, 6.56 mmol) and 1M lithium hydroxide (314 mg, 13.1 mmol) in tetrahydrofuran (51 mL) was stirred at room temperature for 24 hours. The solvent was removed in vacuo and the residue was dissolved in water (10 mL) and ethyl acetate (20 mL) was added. The phases were separated and the aqueous phase was acidified to pH 2 using 2M hydrochloric acid solution (3 mL). The aqueous phase was extracted with diethyl ether (2×30 mL). These organic extracts were combined, dried over magnesium sulfate, filtered and concentrated in vacuo to give the desired product as a white solid, 1.03 g (86%).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in water (10 mL)
  3. additionethyl acetate (20 mL) was added
  4. customThe phases were separated
  5. extractionThe aqueous phase was extracted with diethyl ether (2×30 mL)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-438a62fa6e1a43d78a82022541df5aa3
Source dataset
uspto-grants-2010_01
Patent number
US07649002B2

Reaction notes

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