Tributylphosphine → HCID 10161972, compound

HRID 984958Notes

Reaction equation

HRID 984958 reaction equation
C(P(CCCC)CCCC)CCC.[OH:14][C:15]1[CH:16]=[C:17]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:18]=[CH:19][CH:20]=1.[Br:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]2[CH:39]=[CH:38][C:37](/[C:40](/[CH3:44])=[CH:41]/[CH2:42]O)=[CH:36][CH:35]=2)=[CH:30][CH:29]=1>C1COCC1>[CH2:25]([O:24][C:22](=[O:23])[CH2:21][C:17]1[CH:18]=[CH:19][CH:20]=[C:15]([O:14][CH2:42]/[CH:41]=[C:40](/[C:37]2[CH:38]=[CH:39][C:34]([C:31]3[CH:30]=[CH:29][C:28]([Br:27])=[CH:33][CH:32]=3)=[CH:35][CH:36]=2)\[CH3:44])[CH:16]=1)[CH3:26]

Participants

5

Reactant 3

HCID 13831TributylphosphineHCID 572437Ethyl (3-Hydroxyphenyl)acetateHCID 69796253HCID 69796253, compound

Product 1

HCID 10161972HCID 10161972, compoundYield 51.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under a atmosphere of nitrogen, azodicarboxylic dipiperidide (353 mg, 1.4 mmol) was added at 0-5° C. to a stirred solution of tributylphosphine (0.4 mL, 1.4 mmol), ethyl 3-hydroxyphenylacetate (120 mg, 0.7 mmol) and (E)-3-(4′-bromo-biphenyl-4-yl)-but-2-en-1-ol (200 mg, 0.7 mmol) in dry THF (10 ml), the mixture stirred for 16 h, filtered and concentrated in vacuo. The crude product was then purified by column chromatography on silica (eluent: 20% ethyl acetate in heptane) to give 168 mg (44%) of the title compound.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. customThe crude product was then purified by column chromatography on silica (eluent: 20% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-89129792f6e0416f9347cc0f1e4c758c
Source dataset
uspto-grants-2005_03
Patent number
US06869967B2

Reaction notes

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