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Potassium Carbonate → HCID 57831397, compound

HRID 1672683
Notes
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Reaction equation

HRID 1672683 reaction equation
[C:1]([CH2:3][CH2:4][CH2:5][CH2:6][CH:7](/[CH:20]=[CH:21]/[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[OH:28])[CH2:8][CH2:9][C:10]1[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:11]=1)#[N:2].[C:29]([C:33]1[CH:40]=[CH:39][C:36]([CH2:37]Br)=[CH:35][CH:34]=1)([CH3:32])([CH3:31])[CH3:30].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:29]([C:33]1[CH:34]=[CH:35][C:36]([CH2:37][O:28][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2/[CH:21]=[CH:20]/[CH:7]([CH2:6][CH2:5][CH2:4][CH2:3][C:1]#[N:2])[CH2:8][CH2:9][C:10]2[CH:11]=[CH:12][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:18][CH:19]=2)=[CH:39][CH:40]=1)([CH3:32])([CH3:30])[CH3:31]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 878361-(Bromomethyl)-4-(1,1-dimethylethyl)benzeneHCID 57831335Methyl E-4-{7-cyano-3-[2-(2-hydroxyphenyl)vinyl]heptyl}benzoate

Product 1

HCID 57831397HCID 57831397, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 1.70 g (3.38 mmol, 75% pure) of methyl 4-{7-cyano-3-[2-(2-hydroxyphenyl)vinyl]heptyl}benzoate from Example 95A in 20 ml of dry acetonitrile is mixed with 1.53 g (7.76 mmol) of 4-(tert-butyl)benzyl bromide and 1.4 g (10.13 mmol) of anhydrous potassium carbonate and heated to reflux for 12 hours. The mixture is then filtered and the filtrate is concentrated to dryness. The resulting crude product is taken up on silica gel and purified by flash chromatography (mobile phase: cyclohexane/ethyl acetate 10:1). 1700 mg (3.12 mmol, 96% purity, 92% yield) of an oil are obtained.

Workup

  1. temperatureheated
  2. temperatureto reflux for 12 hours
  3. filtrationThe mixture is then filtered
  4. concentrationthe filtrate is concentrated to dryness
  5. custompurified by flash chromatography (mobile phase: cyclohexane/ethyl acetate 10:1)
  6. custom1700 mg (3.12 mmol, 96% purity, 92% yield) of an oil are obtained

Sources & evidence

ORD record
ord-46a2339d34a1451f8db9dafcb1bbc647
Source dataset
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07998988B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes