Iodoethane → HCID 21279133, compound

HRID 2291629Notes

Reaction equation

HRID 2291629 reaction equation
[OH:1][C:2]1[C:6](=[O:7])[O:5][CH:4]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])[C:3]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[CH2:20](I)[CH3:21].C(=O)([O-])[O-].[K+].[K+].ClCCl>CN(C)C=O.O>[CH2:20]([O:1][C:2]1[C:6](=[O:7])[O:5][CH:4]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])[C:3]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH3:21]

Participants

7

Reactant 4

HCID 6340IodoethaneHCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 13907273HCID 13907273, compound

Product 1

HCID 21279133HCID 21279133, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of methyl 3-(4-hydroxy-5-oxo-3-phenyl2,5-dihydro-2-furyl)propionate (262 mg), ethyl iodide (234 mg) and potassium carbonate (207 mg) in dimethylformamide (3 ml) was stirred for 3.5 hours at ambient temperature. The mixture was poured into a mixture of dichloromethane (10 ml) and water (10 ml). The separated organic layer was washed with water three times, dried and evaporated to dryness. The oily residue was purified by column chromatography on silica gel (8 g, elution by benzene) to yield methyl 3-(4- ethoxy-5-oxo-3-phenyl-2,5-dihydro-2-furyl)propionate (0.20 g) as an oil.

Workup

  1. washThe separated organic layer was washed with water three times
  2. customdried
  3. customevaporated to dryness
  4. customThe oily residue was purified by column chromatography on silica gel (8 g, elution by benzene)

Sources & evidence

ORD record
ord-9c2f11ce2f914374a0861cc0d95df0b7
Source dataset
uspto-grants-1989_01
Patent number
US04797417

Reaction notes

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