Potassium Carbonate → Methyl 4-((3E)-2-[2-(4-cyanophenyl)ethyl]-4-{2-[(5-phenylpentyl)oxy]phenyl}but-3-en-1-yl)benzoate

HRID 1913762Notes

Reaction equation

HRID 1913762 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(=O)([O-])[O-].[K+].[K+].[C:19]([C:21]1[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][CH:29](/[CH:41]=[CH:42]/[C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=2[OH:49])[CH2:30][C:31]2[CH:40]=[CH:39][C:34]([C:35]([O:37][CH3:38])=[O:36])=[CH:33][CH:32]=2)=[CH:23][CH:22]=1)#[N:20]>C(#N)C>[C:19]([C:21]1[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][CH:29](/[CH:41]=[CH:42]/[C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=2[O:49][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:30][C:31]2[CH:32]=[CH:33][C:34]([C:35]([O:37][CH3:38])=[O:36])=[CH:39][CH:40]=2)=[CH:23][CH:22]=1)#[N:20]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 285561(5-Bromopentyl)benzeneHCID 57831366Methyl E-4-[2-[2-(4-cyanophenyl)ethyl]-4-(2-hydroxyphenyl)but-3-enyl]benzoate

Product 1

HCID 57831394Methyl 4-((3E)-2-[2-(4-cyanophenyl)ethyl]-4-{2-[(5-phenylpentyl)oxy]phenyl}but-3-en-1-yl)benzoateYield 99.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

464.2 mg (2.04 mmol) of (5-bromopentyl)benzene and 353.05 mg (2.55 mmol) of potassium carbonate are added to a solution of 700.8 mg (1.7 mmol) of methyl 4-[(3E)-2-[2-(4-cyanophenyl)ethyl]-4-(2-hydroxyphenyl)but-3-en-1-yl]benzoate in 65 ml of acetonitrile, and the mixture is stirred under reflux for 12 hours. After cooling, the potassium carbonate is filtered off and the filtrate is evaporated. The resulting residue is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 7:3). 945 mg (1.7 mmol, 99.5% yield) are obtained.

Workup

  1. temperatureunder reflux for 12 hours
  2. temperatureAfter cooling
  3. filtrationthe potassium carbonate is filtered off
  4. customthe filtrate is evaporated
  5. customThe resulting residue is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 7:3)
  6. custom945 mg (1.7 mmol, 99.5% yield) are obtained

Sources & evidence

ORD record
ord-1dbe816e81a548d48961f1ac6b3cf7fb
Source dataset
uspto-grants-2013_12
Patent number
US08609727B2

Reaction notes

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