Tributylphosphine → HCID 23082914, compound

HRID 2422286Notes

Reaction equation

HRID 2422286 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.[C:14]1([C:20]([C:22]2[CH:23]=[C:24]([CH2:28]O)[CH:25]=[CH:26][CH:27]=2)=[CH2:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1(C)C=CC=CC=1.CCCCCC>[C:14]1([C:20]([C:22]2[CH:23]=[C:24]([CH:25]=[CH:26][CH:27]=2)[CH2:28][O:1][C:2]2[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:6][CH:7]=2)=[CH2:21])[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

7

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 79706Benzenepropanoic acid, 4-hydroxy-, methyl esterHCID 131027423-(1-Phenylethenyl)benzenemethanol

Product 1

HCID 23082914HCID 23082914, compoundYield 86.1%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Procedure

A solution of methyl 3-(4-hydroxyphenyl)propanoate (0.360 g, 2.00 mmol), [3-(1-phenylvinyl)phenyl]methanol (0.421 g, 2.00 mmol) and tributylphosphine (0.747 mL, 3.00 mmol) in toluene (30 mL) was stirred under ice-cooling, 1,1′-(azodicarbonyl)dipiperidine (0.757 g, 3.00 mmol) was added by small portions under a nitrogen atmosphere, and the mixture was stirred at room temperature for 18 hrs. Hexane (15 mL) was added to the reaction mixture, the precipitated insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane-20% ethyl acetate/hexane) to give the title compound as a colorless oil (0.641 g, yield 86%).

Workup

  1. temperaturecooling
  2. filtrationthe precipitated insoluble material was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel chromatography (hexane-20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-9331a3fafa7a4b0bbcae1ff21a61030e
Source dataset
uspto-grants-2011_06
Patent number
US07960369B2

Reaction notes

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