Water → HCID 54365508, compound

HRID 1290217Notes

Reaction equation

HRID 1290217 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:16]=[CH:15][C:7]([CH:8]=[CH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:5]=1.[C:17]([O:20][CH2:21][CH2:22]Br)(=[O:19])[CH3:18].O>CN(C)C=O>[C:17]([O:20][CH2:21][CH2:22][O:3][C:4]1[CH:5]=[CH:6][C:7]([CH:8]=[CH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:15][CH:16]=1)(=[O:19])[CH3:18]

Participants

6

Reactant 4

HCID 962WaterHCID 135641-Acetoxy-2-bromoethaneHCID 24758Sodium hydrideHCID 349172P-hydroxyl ethyl cinnaMate

Product 1

HCID 54365508HCID 54365508, compoundYield 98.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium hydride (60% active, 124 mg) in dimethylformamide (2 ml) at ambient temperature was added ethyl 4-hydroxycinnamate (500 mg) under nitrogen, and the mixture was stirred for 1 hour. 2-Bromoethyl acetate (522 mg) was added to the mixture at same temperature, and the mixture was allowed to stand for 19 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel eluting with chloroform to give ethyl 4-(2-acetoxyethoxy)cinnamate (716 mg) as an oil.

Workup

  1. waitto stand for 19 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was chromatographed on silica gel eluting with chloroform

Sources & evidence

ORD record
ord-3c83735eebca4907a726c058146b6ef1
Source dataset
uspto-grants-1998_05
Patent number
US05750699

Reaction notes

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