Tributylphosphine → HCID 10178071, compound

HRID 984953Notes

Reaction equation

HRID 984953 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.C(P(CCCC)CCCC)CCC.[CH:26]1[C:38]2[CH2:37][C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[C:30]=2[CH:29]=[CH:28][C:27]=1/[C:39](/[CH3:43])=[CH:40]/[CH2:41]O>C1C=CC=CC=1.O.C(OCC)(=O)C>[CH3:12][O:11][C:9](=[O:10])[CH2:8][C:5]1[CH:4]=[CH:3][C:2]([O:1][CH2:41]/[CH:40]=[C:39](/[C:27]2[CH:28]=[CH:29][C:30]3[C:31]4[C:36](=[CH:35][CH:34]=[CH:33][CH:32]=4)[CH2:37][C:38]=3[CH:26]=2)\[CH3:43])=[CH:7][CH:6]=1

Participants

7

Reactant 3

HCID 13831TributylphosphineHCID 518900Benzeneacetic acid, 4-hydroxy-, methyl esterHCID 69792999HCID 69792999, compound

Product 1

HCID 10178071HCID 10178071, compoundYield 62.4%

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Under a atmosphere of nitrogen, methyl 4-hydroxyphenylacetate (183 mg, 1.1 mmol) was added to a stirred cooled solution of azodicarboxylic dipiperidide (378 mg, 1.5 mmol), tributylphosphine (304 mg, 1.5 mmol) and (E)-3-(9H-fluoren-2-yl)-but-2-en-1-ol (236 mg, 1.0 mmol) in dry benzene (30 ml), the mixture warmed to room temperature, and stirred for 17 h. The reaction mixture was diluted with water (100 ml) and ethyl acetate (100 ml each). The aqueous layer was collected and further extracted with ethyl acetate (2×50 ml). The organic layers were combined, washed with brine, dried (MgSO4) and evaporated. The crude product was then purified by column chromatography on silica (eluent: 15% ethyl acetate in toluene) to give 240 mg (62%) of the title compound.

Workup

  1. customThe aqueous layer was collected
  2. extractionfurther extracted with ethyl acetate (2×50 ml)
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe crude product was then purified by column chromatography on silica (eluent: 15% ethyl acetate in toluene)

Sources & evidence

ORD record
ord-cbf15d85c9d04912b156ed6a51975613
Source dataset
uspto-grants-2005_03
Patent number
US06869967B2

Reaction notes

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