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

HRID 1672666Notes

Reaction equation

HRID 1672666 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}benzoateYield 90%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 1150 mg (2.79 mmol) of methyl E-4-[3-(4-cyanobenzyl)-5-(2-hydroxyphenyl)pent-4-enyl]benzoate from Example 75A in 50 ml of dry acetonitrile is mixed with 908 mg (3.35 mmol) of 4-chloromethyl-4′-trifluoromethylbiphenyl from Example 23A and 579 mg (4.19 mmol) of anhydrous potassium-carbonate and heated to 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). 1620 mg (2.51 mmol, 90% yield) of a solid are obtained.

Workup

  1. temperatureheated
  2. temperatureto 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)

Sources & evidence

ORD record
ord-ec079f008ae24057bcdda73e7c1cb1bf
Source dataset
uspto-grants-2011_08
Patent number
US07998988B2

Reaction notes

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