Potassium Carbonate → ethyl(E)-3-(4-pyrrolidin-1-ylmethylphenyl)acrylate

HRID 735164Notes

Reaction equation

HRID 735164 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5][CH:4]=1.[NH:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[N:16]1([CH2:2][C:3]2[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5][CH:4]=2)[CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 31268PyrrolidineHCID 12870366Ethyl 4-bromomethylcinnamate

Product 1

HCID 68817431ethyl(E)-3-(4-pyrrolidin-1-ylmethylphenyl)acrylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2 g (7.43 mmol) of ethyl (E)-3-(4-bromomethylphenyl)acrylate is added to a suspension of 0.69 mL (8.2 mmol) of pyrrolidine and 2.05 g (14.86 mmol) of potassium carbonate in 40 mL of DMF and stirred for 18 hours at ambient temperature. The reaction mixture is evaporated down and the residue is extracted with water and ethyl acetate. The organic phase is dried over sodium sulfate, evaporated down, and the residue is purified by column chromatography on silica gel (eluant: dichloromethane/methanol/ammonia (90:10:1)). Yield: 0.3 g (15.6% of theory); C16H21NO2 (M=259.35); calc.: molecular ion peak (M+H)+: 260; found: molecular ion peak (M+H)+: 260; Rf value: 0.5 (silica gel, dichloromethane/methanol/ammonia (90:10:1)).

Workup

  1. customThe reaction mixture is evaporated down
  2. extractionthe residue is extracted with water and ethyl acetate
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. customevaporated down
  5. customthe residue is purified by column chromatography on silica gel (eluant: dichloromethane/methanol/ammonia (90:10:1))

Sources & evidence

ORD record
ord-243a7e4db4fe485388bb3c06f6236157
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

Loading…