Potassium Carbonate → Methyl 4-[(3E)-2-[2-(4-cyanophenyl)ethyl]-4-(2-{[4-(2-phenylethyl)benzyl]oxy}phenyl)but-3-en-1-yl]benzoate

HRID 1913763Notes

Reaction equation

HRID 1913763 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].[C:23]([C:25]1[CH:30]=[CH:29][C:28]([CH2:31][CH2:32][CH:33](/[CH:45]=[CH:46]/[C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=2[OH:53])[CH2:34][C:35]2[CH:44]=[CH:43][C:38]([C:39]([O:41][CH3:42])=[O:40])=[CH:37][CH:36]=2)=[CH:27][CH:26]=1)#[N:24]>C(#N)C>[C:23]([C:25]1[CH:30]=[CH:29][C:28]([CH2:31][CH2:32][CH:33](/[CH:45]=[CH:46]/[C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=2[O:53][CH2:2][C:3]2[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:5][CH:4]=2)[CH2:34][C:35]2[CH:36]=[CH:37][C:38]([C:39]([O:41][CH3:42])=[O:40])=[CH:43][CH:44]=2)=[CH:27][CH:26]=1)#[N:24]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27339904-Phenethylbenzyl chlorideHCID 57831366HCID 57831366, compound

Product 1

HCID 59180519Methyl 4-[(3E)-2-[2-(4-cyanophenyl)ethyl]-4-(2-{[4-(2-phenylethyl)benzyl]oxy}phenyl)but-3-en-1-yl]benzoateYield 70%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

460 mg (2 mmol) of 1-(chloromethyl)-4-(2-phenylethyl)benzene [preparation according to M. Carrara et al., Arzneim. Forsch. 47 (7), 803-809 (1997)] and 414 mg (3 mmol) of anhydrous potassium carbonate are added to a solution of 411 mg (1 mmol) of methyl 4-[(3E)-2-[2-(4-cyanophenyl)ethyl]-4-(2-hydroxyphenyl)but-3-en-1-yl]benzoate in 10 ml of dry acetonitrile, and the mixture is heated under reflux for 12 hours. The mixture is then evaporated to dryness. The residue is taken up in ethyl acetate, washed with water and with saturated sodium chloride solution and dried over sodium sulphate. After filtration, the organic phase is evaporated and the resulting crude product is purified by preparative HPLC. 431 mg (0.7 mmol, 65% yield) of a solid are obtained.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 12 hours
  3. customThe mixture is then evaporated to dryness
  4. washwashed with water and with saturated sodium chloride solution
  5. dry with materialdried over sodium sulphate
  6. filtrationAfter filtration
  7. customthe organic phase is evaporated
  8. customthe resulting crude product is purified by preparative HPLC

Sources & evidence

ORD record
ord-6e3b0143a7e64b6aa9a59d81e3c223a8
Source dataset
uspto-grants-2013_12
Patent number
US08609727B2

Reaction notes

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