Lithium Hydroxide → HCID 66896499, compound

HRID 1394588Notes

Reaction equation

HRID 1394588 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][CH2:31][CH2:32][F:33])=[CH:14][CH:15]=[CH:16][C:10]=2[CH:9]=1)[CH3:7])C.C1COCC1.[Li+].[OH-]>CO>[F:33][CH2:32][CH2:31][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 69219949HCID 69219949, compound

Product 1

HCID 66896499HCID 66896499, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 0.450 mmol of 3-{7-[2-(3-fluoropropoxy)-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-(3-Fluoropropoxy)-3,5-diisopropylphenyl]-benzo[b]furan-2-yl}-but-2-enoic acid was isolated as a white solid. 1H-NMR (CDCl3),: 7.58 (d, J=6.7 Hz, 1H, Ar—H), 7.56 (d, J=6.2 Hz, 1H, Ar—H), 7.29 (t, J=7.6 Hz, 1H, Ar—H), 7.28 (d, J=2.2 Hz, 1H, Ar—H), 7.17 (d, J=2.1 Hz, 1H, Ar—H), 7.11 (s, 1H, furan-H), 6.59 (s, 1H, C═C—H), 4.25 (dt, J=47.1 Hz, J=6.1 Hz, 2H, O—CH2—CH2—CH2F), 3.46 (t, J=5.9 Hz, 2H, O—CH2—CH2—CH2F), 3.38 (m, 1H, CH3—CH—CH3), 2.95 (m, 1H, CH3—CH—CH3), 2.56 (s, 3H, C═C—CH3), 1.70 (m, 2H, O—CH2—CH2—CH2F), 1.32 (d, J=5.7 Hz, 6H, CH3—CH—CH3), 1.30 (d, J=6.6 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-4677d3de562c4c57826b9c97859b9d16
Source dataset
uspto-grants-2008_03
Patent number
US07348359B2

Reaction notes

Loading…