Tributylphosphine → (Z)-{4-[3-(4-Bromo-phenyl)-3-phenyl-allyloxy]-phenyl}-acetic Acid Methyl Ester

HRID 984949Notes

Reaction equation

HRID 984949 reaction equation
C(P(CCCC)CCCC)CCC.[OH:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][C:22]([O:24][CH3:25])=[O:23])=[CH:17][CH:16]=1.[Br:26][C:27]1[CH:32]=[CH:31][C:30](/[C:33](/[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[CH:34]\[CH2:35]O)=[CH:29][CH:28]=1>C1COCC1>[CH3:25][O:24][C:22](=[O:23])[CH2:21][C:18]1[CH:17]=[CH:16][C:15]([O:14][CH2:35]/[CH:34]=[C:33](\[C:30]2[CH:29]=[CH:28][C:27]([Br:26])=[CH:32][CH:31]=2)/[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 13831TributylphosphineHCID 518900Benzeneacetic acid, 4-hydroxy-, methyl esterHCID 22270289(Z)-3-(4-bromo-phenyl)-3-phenyl-prop-2-en-1-ol

Product 1

HCID 10113944(Z)-{4-[3-(4-Bromo-phenyl)-3-phenyl-allyloxy]-phenyl}-acetic Acid Methyl EsterYield 74.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Azodicarboxylic dipiperidide (0.756 g, 3.0 mmol) was added at 0-5° C. to a stirred solution of tributylphosphine (0.94 ml, 786 mg, 3.0 mmol), methyl 4-hydroxyphenylacetate (332 mg, 2.0 mmol) and (Z)-3-(4-bromo-phenyl)-3-phenyl-prop-2-en-1-ol (578 mg, 2.0 mmol) in dry THF (25 ml), the mixture was stirred for 1 h. The mixture was filtered and concentrated I vacuo. The residue was purified by flash chromatography on silica gel (toluene as eluent) to give 650 mg (74%) of the title compound.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated I vacuo
  3. customThe residue was purified by flash chromatography on silica gel (toluene as eluent)

Sources & evidence

ORD record
ord-2d6d895edd5d4ab9baa1c72d32780d67
Source dataset
uspto-grants-2005_03
Patent number
US06869967B2

Reaction notes

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