Dimethylformamide → HCID 54556949, compound

HRID 2286799Notes

Reaction equation

HRID 2286799 reaction equation
[CH:1]([CH:4]([CH:8]=[CH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:5]([OH:7])=[O:6])([CH3:3])[CH3:2].CN(C=O)C.C(=O)([O-])[O-].[K+].[K+].[C:27]1([C:33]([C:35]2[CH:36]=[C:37]([CH:40]=[CH:41][CH:42]=2)[CH2:38]Br)=[O:34])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CCOCC.O.C1COCC1>[CH:1]([CH:4]([CH:8]=[CH:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:5]([O:7][CH2:38][C:37]1[CH:40]=[CH:41][CH:42]=[C:35]([C:33]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:34])[CH:36]=1)=[O:6])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 895863-(Bromomethyl)benzophenoneHCID 54517208HCID 54517208, compound

Product 1

HCID 54556949HCID 54556949, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21584184Diethylether waterSolvent

Procedure

To a mixture of 2-isopropyl-4-phenyl-3-butenoic acid (0.22 g, 1.07 mmol), 2 ml DMF, 3 ml THF and potassium carbonate (0.23 g, 1.66 mmol) is added m-phenylcarbonylbenzyl bromide (0.33 g, 1.2 mmol). The reaction mixture is stirred overnight at RT and then ether/water is added. The ether phase is washed with 5% NaOH, water and brine, dried over sodium sulfate and concentrated under vacuum. The crude product is plated on silica gel plates eluting with 10% ether/hexane to yield m-phenylcarbonylbenzyl 2-isopropyl-4-phenyl-3-butenoate, MS m/e 398.3 (M+).

Workup

  1. washThe ether phase is washed with 5% NaOH, water and brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated under vacuum
  4. washeluting with 10% ether/hexane

Sources & evidence

ORD record
ord-7ba6b1c7d366439dbdce328ec41b59c6
Source dataset
uspto-grants-1981_05
Patent number
US04267359

Reaction notes

Loading…