Methanol → HCID 58934461, compound

HRID 854866Notes

Reaction equation

HRID 854866 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[O:8][CH:7]([C:14]([F:17])([F:16])[F:15])[C:6]([C:18]([O:20]CC)=[O:19])=[CH:5]2.CO.O.O[Li].O>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[O:8][CH:7]([C:14]([F:17])([F:15])[F:16])[C:6]([C:18]([OH:20])=[O:19])=[CH:5]2

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 69518209HCID 69518209, compound

Product 1

HCID 58934461HCID 58934461, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The ester from Step 2 (4 g, 12 mmole) was dissolved in a mixture of THF:MeOH:H2O and LiOH.H2O (4 g, 95 mmole) was added and the mixture was stirred for 2 h at room temperature and then concentrated in vacuo. The mixture was acidified with 10% HCl and extracted with EtOAc. The EtOAc layer was washed twice with H2O, aqueous NH4Cl solution, dried over Na2SO4 concentrated in vacuo and to give 1.3 g (36% yield) of the product: 1H NMR (CDCl3/300 MHz) 7.48 (s, 1), 7.09 (s, 1H), 6.47 (s, 1H), 5.56 (q, 1H, J=6.9 Hz), 3.79 (s, 3H); ESHRMS m/z 307.0012 (M−H, C12H7ClF3O4, Calc'd 306.9985).

Workup

  1. concentrationconcentrated in vacuo
  2. extractionextracted with EtOAc
  3. washThe EtOAc layer was washed twice with H2O, aqueous NH4Cl solution
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3067a7cc230f426c856823e437d6f3c2
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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