1,4-Dibromobutane → Methyl 4-[(4E)-5-[2-(4-bromobutoxy)phenyl]-3-(4-cyanobenzyl)pent-4-en-1-yl]benzoate

HRID 1913797Notes

Reaction equation

HRID 1913797 reaction equation
[C:1]([C:3]1[CH:31]=[CH:30][C:6]([CH2:7][CH:8](/[CH:21]=[CH:22]/[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[OH:29])[CH2:9][CH2:10][C:11]2[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=2)=[CH:5][CH:4]=1)#[N:2].[Br:32][CH2:33][CH2:34][CH2:35][CH2:36]Br.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Br:32][CH2:33][CH2:34][CH2:35][CH2:36][O:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1/[CH:22]=[CH:21]/[CH:8]([CH2:7][C:6]1[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:31][CH:30]=1)[CH2:9][CH2:10][C:11]1[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 80561,4-DibromobutaneHCID 11430Potassium CarbonateHCID 57831354methyl E-4-[3-(4-cyanobenzyl)-5-(2-hydroxyphenyl)pent-4-enyl]benzoate

Product 1

HCID 59180489Methyl 4-[(4E)-5-[2-(4-bromobutoxy)phenyl]-3-(4-cyanobenzyl)pent-4-en-1-yl]benzoate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 664 mg (1.62 mmol) of methyl E-4-[3-(4-cyanobenzyl)-5-(2-hydroxyphenyl)pent-4-enyl]benzoate (enantiomer 1, Example 51A) in 28 ml of dry acetonitrile is mixed with 1743 mg (8.07 mmol) of 1,4-dibromobutane and 446 mg (3.23 mmol) of anhydrous potassium carbonate and then heated under reflux for 12 h. The mixture is subsequently filtered, and the filtrate is evaporated to dryness. The residue is purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 10:1). 790 mg (1.44 mmol, 89% of theory) of a colourless oil are isolated.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 12 h
  3. filtrationThe mixture is subsequently filtered
  4. customthe filtrate is evaporated to dryness
  5. customThe residue is purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 10:1)
  6. custom790 mg (1.44 mmol, 89% of theory) of a colourless oil are isolated

Sources & evidence

ORD record
ord-ef7dd875e5044d2ba0688d02141c0ad8
Source dataset
uspto-grants-2013_12
Patent number
US08609727B2

Reaction notes

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