Tributylphosphine → HCID 10161128, compound

HRID 984960Notes

Reaction equation

HRID 984960 reaction equation
[CH2:1](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]2[CH:38]=[CH:37][C:36]([CH2:39]/[CH:40]=[CH:41]/CO)=[CH:35][CH:34]=2)=[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][CH2:41]/[CH:40]=[C:39](/[C:36]2[CH:35]=[CH:34][C:33]([C:30]3[CH:29]=[CH:28][C:27]([Br:26])=[CH:32][CH:31]=3)=[CH:38][CH:37]=2)\[CH3:1])=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 13831TributylphosphineHCID 518900Benzeneacetic acid, 4-hydroxy-, methyl esterHCID 22509457HCID 22509457, compound

Product 1

HCID 10161128HCID 10161128, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under an 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), methyl 4-hydroxyphenylacetate (110 mg, 0.7 mmol) and (E)-4-(4′-Bromo-biphenyl-4-yl)-but-2-en-1-ol (example 22 step A-B)(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 264 mg (84%) 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-febd4da4d51940d889e66e0a397b4b23
Source dataset
uspto-grants-2005_03
Patent number
US06869967B2

Reaction notes

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