Potassium Carbonate → HCID 59180522, compound

HRID 1913795Notes

Reaction equation

HRID 1913795 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[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=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:23]=[CH:24]/[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[O:31][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=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:5][CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 561788(6-Bromohexyl)benzeneHCID 57831366Methyl E-4-[2-[2-(4-cyanophenyl)ethyl]-4-(2-hydroxyphenyl)but-3-enyl]benzoate

Product 1

HCID 59180522HCID 59180522, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 200 mg (0.49 mmol) of methyl 4-[(3E)-2-[2-(4-cyanophenyl)ethyl]-4-(2-hydroxyphenyl)but-3-en-1-yl]benzoate in 25 ml of acetonitrile is mixed with 176 mg (0.73 mmol) of (6-bromohexyl)benzene and 101 mg (0.73 mmol) of potassium carbonate and then stirred under reflux for 12 h. After cooling, the potassium carbonate is filtered off and the filtrate is evaporated. 364 mg (0.48 mmol, 98% of theory, purity 76%) of a yellowish oil are obtained.

Workup

  1. temperatureunder reflux for 12 h
  2. temperatureAfter cooling
  3. filtrationthe potassium carbonate is filtered off
  4. customthe filtrate is evaporated
  5. custom364 mg (0.48 mmol, 98% of theory, purity 76%) of a yellowish oil are obtained

Sources & evidence

ORD record
ord-b96738d2b53d41498720b2a417fd945d
Source dataset
uspto-grants-2013_12
Patent number
US08609727B2

Reaction notes

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