Potassium Carbonate → HCID 57965768, compound

HRID 1920587Notes

Reaction equation

HRID 1920587 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+].[CH2:19]([O:21][C:22](=[O:50])[CH2:23][C:24]1([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)[CH2:26][CH2:25]1)[CH3:20]>C(#N)C>[CH2:19]([O:21][C:22](=[O:50])[CH2:23][C:24]1([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)[CH2:25][CH2:26]1)[CH3:20]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 285561(5-Bromopentyl)benzeneHCID 57965750Methyl 4-[(3E)-2-{2-[1-(2-ethoxy-2-oxoethyl)cyclopropyl]ethyl}-4-(2-hydroxyphenyl)but-3-en-1-yl]benzoate

Product 1

HCID 57965768HCID 57965768, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

273 mg (1.2 mmol) of (5-bromopentyl)benzene and 222 mg (1.6 mmol) of anhydrous potassium carbonate are added to a solution of 350 mg (0.8 mmol) of methyl 4-[(3E)-2-{2-[1-(2-ethoxy-2-oxoethyl)cyclopropyl]ethyl}-4-(2-hydroxyphenyl)but-3-en-1-yl]benzoate in 10 ml of dry acetonitrile, and the mixture is heated under reflux for 12 hours. The mixture is then concentrated to dryness. The residue is taken up in ethyl acetate, washed with water and saturated sodium chloride solution and dried over sodium sulfate. The organic phase is concentrated. The crude product obtained is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 9:1). This gives 275 mg (58% of theory) of a solid.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 12 hours
  3. concentrationThe mixture is then concentrated to dryness
  4. washwashed with water and saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. concentrationThe organic phase is concentrated

Sources & evidence

ORD record
ord-61c1fd998df74cd0ba0255c9063d28a4
Source dataset
uspto-grants-2012_05
Patent number
US08168821B2

Reaction notes

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