Triphenylphosphine → 5-[2-(2,6-Dimethyl-4'-trifluoromethyl-biphenyl-4-yloxy)-1,1-dimethyl-ethyl]-thiophene-2-carboxylic acid methyl ester

HRID 660986Notes

Reaction equation

HRID 660986 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:10]([CH3:14])([CH3:13])[CH2:11][OH:12])=[CH:8][CH:9]=1)=[O:4].[CH3:15][C:16]1[CH:21]=[C:20](O)[CH:19]=[C:18]([CH3:23])[C:17]=1[C:24]1[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1(C)C=CC=CC=1.CO>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:10]([CH3:14])([CH3:13])[CH2:11][O:12][C:20]2[CH:21]=[C:16]([CH3:15])[C:17]([C:24]3[CH:29]=[CH:28][C:27]([C:30]([F:31])([F:33])[F:32])=[CH:26][CH:25]=3)=[C:18]([CH3:23])[CH:19]=2)=[CH:8][CH:9]=1)=[O:4]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 569717492,6-Dimethyl-4'-(trifluoromethyl)-[1,1'-biphenyl]-4-olHCID 67484466Methyl 5-(1-hydroxy-2-methylpropan-2-yl)thiophene-2-carboxylate

Product 1

HCID 593559295-[2-(2,6-Dimethyl-4'-trifluoromethyl-biphenyl-4-yloxy)-1,1-dimethyl-ethyl]-thiophene-2-carboxylic acid methyl esterYield 42%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 5-(2-hydroxy-1,1-dimethyl-ethyl)-thiophene-2-carboxylic acid methyl ester (0.436 g, 2.04 mmol), 2,6-dimethyl-4′-trifluoromethyl-biphenyl-4-ol (0.596 g, 2.24 mmol), and PPh3 (0.793 g, 3.02 mmol) is dissolved in toluene (20 mL), treated with 1,1′-(azodicarbonyl)dipiperidine (ADDP, 0.763 g, 3.02 mmol), and stirred overnight at 80° C. The mixture is then cooled to rt, diluted with MeOH until homogeneous, and concentrated. The residue is loaded onto silica gel and eluted using hexanes with an ethyl acetate gradient from 0% to 40% to afford 5-[2-(2,6-dimethyl-4′-trifluoromethyl-biphenyl-4-yloxy)-1,1-dimethyl-ethyl]-thiophene-2-carboxylic acid methyl ester (0.394 g, 42%). MS (ES): 463.3 [M+H]+.

Workup

  1. temperatureThe mixture is then cooled to rt
  2. concentrationconcentrated
  3. washeluted

Sources & evidence

ORD record
ord-996cda2a683641c991574375c43bd1dd
Source dataset
uspto-grants-2011_12
Patent number
US08084489B2

Reaction notes

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