Ethanol → HCID 10274756, compound

HRID 984959Notes

Reaction equation

HRID 984959 reaction equation
C([O:3][C:4](=[O:30])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([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: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:8]3[CH:7]=[C:6]([CH2:5][C:4]([OH:30])=[O:3])[CH:11]=[CH:10][CH:9]=3)=[CH:22][CH:21]=2)=[CH:24][CH:25]=1

Participants

6

Reactant 2

HCID 702EthanolHCID 10161972HCID 10161972, compound

Product 1

HCID 10274756HCID 10274756, compoundYield 98.6%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Procedure

(E)-{3-[3-(4′-Bromo-biphenyl-4-yl)-but-2-enyloxy]-phenyl}-acetic acid ethyl ester (example 22) (150 mg, 0.32 mmol) was suspended in 1N NaOH (0.82 mL) and ethanol (5 mL) and stirred for 24 h at room temperature. The mixture was diluted with 1N HCl (0.82 mL) and ethyl acetate (10 mL). The aqueous layer was separated and extracted with ethyl acetate (20 mL) The organic layers were combined, washed with brine, dried (MgSO4) and evaporated to give 138 mg (98%) of the title compound.

Workup

  1. customThe aqueous layer was separated
  2. extractionextracted with ethyl acetate (20 mL) The organic layers
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-daaae1a3425647e4b8c97e460f67e11f
Source dataset
uspto-grants-2005_03
Patent number
US06869967B2

Reaction notes

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