Tributylphosphine → HCID 20768015, compound

HRID 984951Notes

Reaction equation

HRID 984951 reaction equation
C(P(CCCC)CCCC)CCC.[CH2:14]([O:16][C:17](=[O:27])[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[C:21]([Cl:26])[CH:20]=1)[CH3:15].[Br:28][C:29]1[CH:34]=[CH:33][C:32](/[C:35](/[C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)=[CH:36]/[CH2:37]O)=[CH:31][CH:30]=1>C1COCC1>[CH2:14]([O:16][C:17](=[O:27])[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:37]/[CH:36]=[C:35](/[C:32]2[CH:31]=[CH:30][C:29]([Br:28])=[CH:34][CH:33]=2)\[C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)=[C:21]([Cl:26])[CH:20]=1)[CH3:15]

Participants

5

Reactant 3

HCID 13831TributylphosphineHCID 11031224Ethyl 3-chloro-4-hydroxyphenylacetateHCID 67146538HCID 67146538, compound

Product 1

HCID 20768015HCID 20768015, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under a atmosphere of nitrogen, azodicarboxylic dipiperidide (756 mg, 3.0 mmol) was added at 0-5° C. to a stirred solution of tributylphosphine (786 mg, 3.0 mmol), 3-chloro-4-hydroxyphenyl-acetic acid ethyl ester (537 mg, 2.5 mmol) and (E)-3-(4-bromo-phenyl)-3-phenyl-prop-2-en-1-ol (578 mg, 2.0 mmol) in dry THF (15 ml), the mixture was stirred for 2 h. The reaction mixture was filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica (eluent: toluen) to give 640 mg (66%) of the title compound.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by flash chromatography on silica (eluent: toluen)

Sources & evidence

ORD record
ord-cb6eb1befa03455296175ddf063cadcb
Source dataset
uspto-grants-2005_03
Patent number
US06869967B2

Reaction notes

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