Tributylphosphine → 3-{4-[3,3-Bis-(4-bromo-phenyl)-allyloxy]-phenyl}-propionic Acid Ethyl Ester

HRID 984939Notes

Reaction equation

HRID 984939 reaction equation
C(P(CCCC)CCCC)CCC.[CH2:14]([O:16][C:17](=[O:27])[CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1)[CH3:15].[Br:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]([C:39]2[CH:44]=[CH:43][C:42]([Br:45])=[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][CH2:19][C:20]1[CH:21]=[CH:22][C:23]([O:26][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:40]=[CH:41][C:42]([Br:45])=[CH:43][CH:44]=2)=[CH:24][CH:25]=1)[CH3:15]

Participants

5

Reactant 3

HCID 13831TributylphosphineHCID 2736435Ethyl 4-hydroxyhydrocinnamateHCID 222703043,3-Bis-(4-bromophenyl)prop-2-en-1-ol

Product 1

HCID 102092253-{4-[3,3-Bis-(4-bromo-phenyl)-allyloxy]-phenyl}-propionic Acid Ethyl EsterYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under a atmosphere of nitrogen, azodicarboxylic dipiperidide (504 mg, 2.0 mmol) was added at 0-5° C. to a stirred solution of tributylphosphine (404 mg, 2.0 mmol), 3-(4-hydroxy-phenyl)-propionic acid ethyl ester (388 mg, 2.0 mmol) and 3,3-bis-(4-bromophenyl)prop-2-en-1-ol (736 mg, 2.0 mmol) in dry THF (50 ml), the mixture warmed to room temperature, and stirred for 4 h. The reaction mixture was concentrated in vacuo, and added water and ethyl acetate (75 ml each). The aqueous layer was collected and further extracted with ethyl acetate (2×75 ml). The organic layers were combined, washed with water, dried (MgSO4) and evaporated. The crude product was then purified by column chromatography on silica (25% ethylacetane in heptane eluent) to give 1.0 g (92%) of the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionadded water and ethyl acetate (75 ml each)
  3. customThe aqueous layer was collected
  4. extractionfurther extracted with ethyl acetate (2×75 ml)
  5. washwashed with water
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customThe crude product was then purified by column chromatography on silica (25% ethylacetane in heptane eluent)

Sources & evidence

ORD record
ord-6853d51972124cdb8e5f98c5182e8d92
Source dataset
uspto-grants-2005_03
Patent number
US06869967B2

Reaction notes

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