Potassium Carbonate → Methyl E-4-{3-(4-cyanobenzyl)-5-[2-(4'-trifluoromethylbiphenyl-4-ylmethoxy)phenyl]pent-4-enyl}benzoate

HRID 1927418Notes

Reaction equation

HRID 1927418 reaction equation
[C:1]([C:3]1[CH:31]=[CH:30][C:6]([CH2:7][CH:8](/[CH:21]=[CH:22]/[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[OH:29])[CH2:9][CH2:10][C:11]2[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=2)=[CH:5][CH:4]=1)#[N:2].Cl[CH2:33][C:34]1[CH:39]=[CH:38][C:37]([C:40]2[CH:45]=[CH:44][C:43]([C:46]([F:49])([F:48])[F:47])=[CH:42][CH:41]=2)=[CH:36][CH:35]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:7][CH:8](/[CH:21]=[CH:22]/[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[O:29][CH2:33][C:34]2[CH:35]=[CH:36][C:37]([C:40]3[CH:45]=[CH:44][C:43]([C:46]([F:47])([F:48])[F:49])=[CH:42][CH:41]=3)=[CH:38][CH:39]=2)[CH2:9][CH2:10][C:11]2[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=2)=[CH:30][CH:31]=1)#[N:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 114599214-(4-Trifluoromethylphenyl)benzylchlorideHCID 57831354methyl E-4-[3-(4-cyanobenzyl)-5-(2-hydroxyphenyl)pent-4-enyl]benzoate

Product 1

HCID 57831398Methyl E-4-{3-(4-cyanobenzyl)-5-[2-(4'-trifluoromethylbiphenyl-4-ylmethoxy)phenyl]pent-4-enyl}benzoate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 300 mg (0.73 mmol) of methyl 4-[(4E)-3-(4-cyanobenzyl)-5-(2-hydroxyphenyl)pent-4-en-1-yl]benzoate in 30 ml of dry acetonitrile is mixed with 236.8 mg (0.87 mmol) of 4-(chloromethyl)-4′-(trifluoromethyl)biphenyl and 151 mg (1.09 mmol) of anhydrous potassium carbonate and heated under reflux for 12 hours. The mixture is then concentrated to dryness. The residue is taken up in ethyl acetate, washed with water and saturated sodium chloride solution and dried over sodium sulfate. The organic phase is concentrated. The resulting crude product is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 7:3). 331 mg (0.51 mmol, 70% of theory) of a solid are obtained.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 12 hours
  3. concentrationThe mixture is then concentrated to dryness
  4. washwashed with water and saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. concentrationThe organic phase is concentrated
  7. customThe resulting crude product is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 7:3)
  8. custom331 mg (0.51 mmol, 70% of theory) of a solid are obtained

Sources & evidence

ORD record
ord-26c7de5956774250b90fa808320963e3
Source dataset
uspto-grants-2012_05
Patent number
US08183271B2

Reaction notes

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