Potassium Carbonate → Methyl E-4-{4-[2-(4-bromobenzyloxy)phenyl]-2-[2-(4-cyanophenyl)ethyl]but-3-enyl}benzoate

HRID 1672620Notes

Reaction equation

HRID 1672620 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH:11](/[CH:23]=[CH:24]/[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[OH:31])[CH2:12][C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=2)=[CH:5][CH:4]=1)#[N:2].[Br:32][C:33]1[CH:40]=[CH:39][C:36]([CH2:37]Br)=[CH:35][CH:34]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Br:32][C:33]1[CH:40]=[CH:39][C:36]([CH2:37][O:31][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2/[CH:24]=[CH:23]/[CH:11]([CH2:10][CH2:9][C:6]2[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)[CH2:12][C:13]2[CH:14]=[CH:15][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:21][CH:22]=2)=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 685274-Bromobenzyl bromideHCID 57831366Methyl E-4-[2-[2-(4-cyanophenyl)ethyl]-4-(2-hydroxyphenyl)but-3-enyl]benzoate

Product 1

HCID 57864403Methyl E-4-{4-[2-(4-bromobenzyloxy)phenyl]-2-[2-(4-cyanophenyl)ethyl]but-3-enyl}benzoateYield 88%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 230 mg (0.56 mmol) of methyl E-4-[2-[2-(4-cyanophenyl)ethyl]-4-(2-hydroxyphenyl)but-3-enyl]benzoate from Example 17A in 5 ml of dry acetonitrile is mixed with 209 mg (0.84 mmol) of 4-bromobenzyl bromide and 116 mg (0.84 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 resulting organic phase is concentrated. The crude product is purified by flash chromatography on silica gel (mobile phase: cyclohexane). 286 mg (0.49 mmol, 88% 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 resulting organic phase is concentrated
  7. customThe crude product is purified by flash chromatography on silica gel (mobile phase: cyclohexane)

Sources & evidence

ORD record
ord-4774bd0da7404992be7397c444953ed0
Source dataset
uspto-grants-2011_08
Patent number
US07998988B2

Reaction notes

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