Triphenylphosphine → 4-[1-Allyl-1-(2,6-dimethyl-4'-trifluoromethyl-biphenyl-4-yloxymethyl)-but-3-enyl]-benzoic acid methyl ester

HRID 658292Notes

Reaction equation

HRID 658292 reaction equation
[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([CH2:16][CH:17]=[CH2:18])([CH2:14][OH:15])[CH2:11][CH:12]=[CH2:13])=[CH:6][CH:5]=1.[CH3:20][C:21]1[CH:26]=[C:25](O)[CH:24]=[C:23]([CH3:28])[C:22]=1[C:29]1[CH:34]=[CH:33][C:32]([C:35]([F:38])([F:37])[F:36])=[CH:31][CH:30]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1(C)C=CC=CC=1.CO>[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([CH2:16][CH:17]=[CH2:18])([CH2:14][O:15][C:25]2[CH:26]=[C:21]([CH3:20])[C:22]([C:29]3[CH:34]=[CH:33][C:32]([C:35]([F:36])([F:38])[F:37])=[CH:31][CH:30]=3)=[C:23]([CH3:28])[CH:24]=2)[CH2:11][CH:12]=[CH2:13])=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 569717492,6-Dimethyl-4'-(trifluoromethyl)-[1,1'-biphenyl]-4-olHCID 674860384-(1-Allyl-1-hydroxymethyl-but-3-enyl)-benzoic acid methyl ester

Product 1

HCID 674857174-[1-Allyl-1-(2,6-dimethyl-4'-trifluoromethyl-biphenyl-4-yloxymethyl)-but-3-enyl]-benzoic acid methyl esterYield 64.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 4-(1-allyl-1-hydroxymethyl-but-3-enyl)-benzoic acid methyl ester (0.768 g, 2.95 mmol), 2,6-dimethyl-4′-trifluoromethyl-biphenyl-4-ol (0.861 g, 3.23 mmol), and triphenylphosphine (1.180 g, 4.50 mmol) in toluene (30 mL) is treated with 1,1′-(azodicarbonyl)-dipiperidine (1.182 g, 4.68 mmol) and stirred overnight at 80° C. The reaction mixture is then cooled to room temperature, diluted with MeOH, and concentrated. The residue is loaded onto silica gel and eluted with hexanes using a gradient of 0% EtOAc to 40% EtOAc to provide 0.964 g (64%) of the title compound as a clear syrup. 1H NMR (CDCl3): δ 8.02-8.00 (m, 2H), 7.67 (d, J=8.0 Hz, 2H), 7.46-7.44 (m, 2H), 7.26 (d, J=7.8 Hz, 2H), 6.68 (s, 2H), 5.60-5.54 (m, 2H), 5.08-5.00 (m, 4H), 4.15 (s, 2H), 3.91 (s, 3H), 2.66 (d, J=7.6 Hz, 4H), 1.99 (s, 6H).

Workup

  1. temperatureThe reaction mixture is then cooled to room temperature
  2. concentrationconcentrated
  3. washeluted with hexanes using a gradient of 0% EtOAc to 40% EtOAc

Sources & evidence

ORD record
ord-c134d679b0244a7ea3b5fdd6bd2b93bb
Source dataset
uspto-grants-2011_12
Patent number
US08076374B2

Reaction notes

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