Lithium Hydroxide → HCID 86594127, compound

HRID 1394590Notes

Reaction equation

HRID 1394590 reaction equation
C([O:3][C:4](=[O:34])[CH:5]=[C:6]([C:8]1[O:12][C:11]2[C:13]([C:17]3[CH:22]=[C:21]([CH:23]([CH3:25])[CH3:24])[CH:20]=[C:19]([CH:26]([CH3:28])[CH3:27])[C:18]=3[O:29][CH2:30][CH:31]([F:33])[F:32])=[CH:14][CH:15]=[CH:16][C:10]=2[CH:9]=1)[CH3:7])C.C1COCC1.[Li+].[OH-]>CO>[F:33][CH:31]([F:32])[CH2:30][O:29][C:18]1[C:19]([CH:26]([CH3:28])[CH3:27])=[CH:20][C:21]([CH:23]([CH3:25])[CH3:24])=[CH:22][C:17]=1[C:13]1[C:11]2[O:12][C:8]([C:6]([CH3:7])=[CH:5][C:4]([OH:34])=[O:3])=[CH:9][C:10]=2[CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 72357130HCID 72357130, compound

Product 1

HCID 86594127HCID 86594127, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 0.450 mmol of 3-{7-[2-(2,2-difluoroethoxy)-3,5-diisopropylphenyl]-benzo[b]furan-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, the crude acid was recrystallized from acetonitrile. 3-{7-[2-(2,2-Difluoroethoxy)-3,5-diisopropylphenyl]-benzo[b]furan-2-yl}-but-2-enoic acid was isolated as a white solid. 1H-NMR (400 MHz, CDCl3) δ 7.60 (d, J=7.1 Hz, 1H, Ar—H), 7.57 (d, J=7.4 Hz, 1H, Ar—H), 7.32 (d, J=2.3 Hz, 1H, Ar—H), 7.31 (t, J=7.6 Hz, 1H, Ar—H), 7.18 (d, J=2.2 Hz, 1H, Ar—H), 7.11 (s, 1H, furan-H), 6.58 (s, 1H, C═C—H), 5.54 (tt, J=55.3 Hz, J=4.2 Hz, 1H, O—CH2—CF2H), 3.54 (dt, J=13.6 Hz, J=4.2 Hz, 2H, O—CH2—CF2H), 3.42 (m, 1H, CH3—CH—CH3), 2.96 (m, 1H, CH3—CH—CH3), 2.57 (s, 3H, C═C—CH3), 1.32 (d, J=6.8 Hz, 6H, CH3—CH—CH3), 1.31 (d, J=6.8 Hz, 6H, CH3—CH—CH3).

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-0d18eed0e1f34417a9f8bba07c88eba9
Source dataset
uspto-grants-2008_03
Patent number
US07348359B2

Reaction notes

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