Dimethylformamide → Ethyl 2-(4-benzyloxyphenyl)-3-(6-bromo-2,3,4,5-tetramethoxyphenyl)-2-ethoxycarbonylpropionate

HRID 2268455

Reaction equation

HRID 2268455 reaction equation
CN(C=O)C.[CH2:6]([O:13][C:14]1[CH:19]=[CH:18][C:17]([CH:20]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:16][CH:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[Br:31][C:32]1[C:37]([CH2:38]Br)=[C:36]([O:40][CH3:41])[C:35]([O:42][CH3:43])=[C:34]([O:44][CH3:45])[C:33]=1[O:46][CH3:47].C(=O)([O-])[O-].[K+].[K+]>O>[CH2:6]([O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([C:26]([O:28][CH2:29][CH3:30])=[O:27])([CH2:38][C:37]2[C:32]([Br:31])=[C:33]([O:46][CH3:47])[C:34]([O:44][CH3:45])=[C:35]([O:42][CH3:43])[C:36]=2[O:40][CH3:41])[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:16][CH:15]=1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 2823246Diethyl 2-(4-(benzyloxy)phenyl)malonateHCID 183486201-Bromo-6-bromomethyl-2,3,4,5-tetramethoxybenzene2×

Product 1

HCID 18348651Ethyl 2-(4-benzyloxyphenyl)-3-(6-bromo-2,3,4,5-tetramethoxyphenyl)-2-ethoxycarbonylpropionateYield 49.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A DMF (120 ml) suspension of ethyl 2-(4-benzyloxyphenyl)-2-ethoxycarbonylacetate (12.0 g, 35.1 mmols), 1-bromo-6-bromomethyl-2,3,4,5-tetramethoxybenzene (16.9 g, 45.6 mmols) and potassium carbonate (14.5 g, 105 mmols) was stirred at room temperature for 6 hours, and then 1-bromo-6-bromomethyl-2,3,4,5-tetramethoxybenzene (2.60 g, 7.02 mmols) was added thereto stirring was continued at room temperature for further 6 hours. Water was added to the reaction mixture, which was then extracted with diethyl ether. The organic layer was washed with water and a saturated aqueous sodium chloride solution, and then dried. The solvent was evaporated out in vacuo, and the resulting crude product was purified by recrystallization (from hexane-ethyl acetate) to obtain the entitled compound (11.0 g) as crystals.

Workup

  1. stirringthereto stirring
  2. waitwas continued at room temperature for further 6 hours
  3. extractionwas then extracted with diethyl ether
  4. washThe organic layer was washed with water
  5. dry with materiala saturated aqueous sodium chloride solution, and then dried
  6. customThe solvent was evaporated out in vacuo
  7. customthe resulting crude product was purified by recrystallization (from hexane-ethyl acetate)

Sources & evidence

ORD record
ord-84c101868c234a6ea17a0a5ae58899ec
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Linked notes

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