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

HRID 1927396Notes

Reaction equation

HRID 1927396 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].[Cl:32][C:33]1[CH:40]=[C:39]([C:41]([CH3:44])([CH3:43])[CH3:42])[CH:38]=[CH:37][C:34]=1[CH2:35]Br.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:41]([C:39]1[CH:38]=[CH:37][C:34]([CH2:35][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)=[C:33]([Cl:32])[CH:40]=1)([CH3:44])([CH3:42])[CH3:43]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 578313342-Chloro-4-(tert-butyl)benzyl bromideHCID 57831366HCID 57831366, compound

Product 1

HCID 57831384Methyl 4-{(3E)-4-{2-[(4-tert-butyl-2-chlorobenzyl)oxy]phenyl}-2-[2-(4-cyanophenyl)ethyl]but-3-en-1-yl}benzoate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 450 mg (1.09 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 is mixed with 825.2 mg (1.64 mmol) of 2-chloro-4-(tert-butyl)benzyl bromide and 453.4 mg (3.28 mmol) of anhydrous potassium carbonate and heated under reflux for 12 h. 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 preparative HPLC. 518 mg (0.87 mmol, 73.9% of theory) of a colorless foam are obtained.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 12 h
  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 preparative HPLC
  8. custom518 mg (0.87 mmol, 73.9% of theory) of a colorless foam are obtained

Sources & evidence

ORD record
ord-107127d7fb91432bae58eba1bf1a2973
Source dataset
uspto-grants-2012_05
Patent number
US08183271B2

Reaction notes

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