Potassium Carbonate → Ethyl (7E)-6-[2-(4-cyanophenyl)ethyl]-8-{2-[(5-phenylpentyl)oxy]phenyl}oct-7-enoate

HRID 1927437Notes

Reaction equation

HRID 1927437 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH:11](/[CH:21]=[CH:22]/[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[OH:29])[CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:5][CH:4]=1)#[N:2].Br[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH:11](/[CH:21]=[CH:22]/[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[O:29][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:5][CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 285561(5-Bromopentyl)benzeneHCID 57831338Ethyl E-6-[2-(4-cyanophenyl)ethyl]-8-(2-hydroxyphenyl)oct-7-enoate

Product 1

HCID 57831356Ethyl (7E)-6-[2-(4-cyanophenyl)ethyl]-8-{2-[(5-phenylpentyl)oxy]phenyl}oct-7-enoate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 127 mg (0.32 mmol) of ethyl (7E)-6-[2-(4-cyanophenyl)ethyl]-8-(2-hydroxyphenyl)oct-7-enoate in 10 ml of acetonitrile is mixed with 88.42 mg (0.39 mmol) of (5-bromopentyl)benzene and 67.25 mg (0.49 mmol) of potassium carbonate and stirred under reflux for 12 hours. After cooling, the mixture is concentrated. The residue is taken up in ethyl acetate and extracted with water. The organic phase is washed with saturated sodium chloride solution, dried over sodium sulfate and concentrated. The resulting residue is purified by preparative HPLC. 128 mg (0.24 mmol, 73.4% of theory) of the title compound are obtained.

Workup

  1. temperatureunder reflux for 12 hours
  2. temperatureAfter cooling
  3. concentrationthe mixture is concentrated
  4. extractionextracted with water
  5. washThe organic phase is washed with saturated sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customThe resulting residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-76b16b5b2083417188cc5ae3740a9008
Source dataset
uspto-grants-2012_05
Patent number
US08183271B2

Reaction notes

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