Lithium Hydroxide → HCID 86594128, compound

HRID 1394600Notes

Reaction equation

HRID 1394600 reaction equation
C([O:3][C:4](=[O:36])[CH:5]=[C:6]([C:8]1[S:12][C:11]2[CH:13]=[CH:14][CH:15]=[C:16]([C:17]3[CH:22]=[C:21]([C:23]([CH3:26])([CH3:25])[CH3:24])[CH:20]=[C:19]([C:27]([CH3:30])([CH3:29])[CH3:28])[C:18]=3[O:31][CH2:32][CH:33]([F:35])[F:34])[C:10]=2[CH:9]=1)[CH3:7])C.C1COCC1.[Li+].[OH-]>CO>[F:35][CH:33]([F:34])[CH2:32][O:31][C:18]1[C:19]([C:27]([CH3:29])([CH3:28])[CH3:30])=[CH:20][C:21]([C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:22][C:17]=1[C:16]1[C:10]2[CH:9]=[C:8]([C:6]([CH3:7])=[CH:5][C:4]([OH:36])=[O:3])[S:12][C:11]=2[CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 72357125HCID 72357125, compound

Product 1

HCID 86594128HCID 86594128, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 0.450 mmol of 3-{4-[2-(2,2-difluoroethoxy)-3,5-di-tert-butylphenyl]-benzo[b]thien-2-yl}-but-2-enoic acid ethyl ester, 3 mL of THF, 3 mL of methanol and 1 mL of LiOH (2N aqueous) was refluxed for 2 hours. After cooling at room temperature, the mixture was acidified to pH=2 and extracted with ethyl acetate. The organic layer was dried over MgSO4 and after evaporation of the solvents, and the crude acid was recrystallized from acetonitrile to afford 192 mg (0.378 mmol, yield: 58%) of 3-{4-[2-(2,2-difluoroethoxy)-3,5-di-tert-butylphenyl]-benzo[b]thien-2-yl}-but-2-enoic acid was isolated as a white solid. 1H NMR (CDCl3), δ: 7.81 (dd, J=7.3, 1.5 Hz, 1H), 7.45 (m, 4H), 7.21 (d, J=2.4 Hz, 1H), 6.33 (s, 1H), 5.19 (dt, J=55.5, 4.3 Hz, 1H), 3.51 (m, 2H), 2.59 (s, 3H), 1.48 (s, 9H), 1.35 (s, 9H).

Workup

  1. temperaturewas refluxed for 2 hours
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over MgSO4
  4. customafter evaporation of the solvents
  5. customthe crude acid was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-cc364e06ae80403cb13bc180fc836083
Source dataset
uspto-grants-2008_03
Patent number
US07348359B2

Reaction notes

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