Ethanol → HCID 10137953, compound

HRID 984961Notes

Reaction equation

HRID 984961 reaction equation
C([O:3][C:4](=[O:30])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13]/[CH:14]=[C:15](/[C:17]2[CH:22]=[CH:21][C:20]([C:23]3[CH:28]=[CH:27][C:26]([Br:29])=[CH:25][CH:24]=3)=[CH:19][CH:18]=2)\[CH3:16])=[CH:8][CH:7]=1)C.C(O)C>[OH-].[Na+].Cl.C(OCC)(=O)C>[Br:29][C:26]1[CH:27]=[CH:28][C:23]([C:20]2[CH:19]=[CH:18][C:17](/[C:15](/[CH3:16])=[CH:14]/[CH2:13][O:12][C:9]3[CH:8]=[CH:7][C:6]([CH2:5][C:4]([OH:30])=[O:3])=[CH:11][CH:10]=3)=[CH:22][CH:21]=2)=[CH:24][CH:25]=1

Participants

6

Reactant 2

HCID 702EthanolHCID 69793069HCID 69793069, compound

Product 1

HCID 10137953HCID 10137953, compoundYield 55.6%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Procedure

(E)-{4-[3-(4′-Bromo-biphenyl-4-yl)-but-2-enyloxy]-phenyl}-acetic acid ethyl ester (example 24) (210 mg, 0.58 mmol) was suspended in 1N NaOH (1.16 mL) and ethanol (5 mL) and stirred for 24 h at room temperature. The mixture was diluted with 1N HCl (1.16 mL) and ethyl acetate (10 mL). The aqueous layer was separated and extracted with ethyl acetate (30 L) The organic layers were combined, washed with brine, dried (MgSO4) and evaporated to give 141 mg (55%) of the title compound.

Workup

  1. customThe aqueous layer was separated
  2. extractionextracted with ethyl acetate (30 L) The organic layers
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-b6308a8855a247e5a57afbba5bf4971a
Source dataset
uspto-grants-2005_03
Patent number
US06869967B2

Reaction notes

Loading…