Pyridine → Butanoic acid, 3-(acetyloxy)-2-methylene-, ethyl ester

HRID 2255655Notes

Reaction equation

HRID 2255655 reaction equation
[OH:1][CH:2]([C:4](=[CH2:10])[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH3:3].N1C=CC=CC=1.[C:17](Cl)(=[O:19])[CH3:18]>ClCCl>[C:17]([O:1][CH:2]([C:4](=[CH2:10])[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH3:3])(=[O:19])[CH3:18]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 10855587Butanoic acid, 3-hydroxy-2-methylene-, ethyl ester

Product 1

HCID 11063122Butanoic acid, 3-(acetyloxy)-2-methylene-, ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 2-(1-hydroxyethyl)acrylate (40 g) and pyridine (26.9 ml) in dichloromethane (277 ml) was added dropwise acetyl chloride (23.7 ml) at 0° C. The reaction mixture was stirred for 1 hour and quenched with water (200 ml). The aqueous layer was separated and extracted twice with dichloromethane. The combined organic layers were washed with 1N hydrochloric acid, saturated aqueous sodium hydrogen carbonate water and an aqueous sodium chloride in turn, and then, dried over magnesium sulfate. After the resultant solution was evaporated, the residue was distilled in vacuo to give ethyl 2-(1-acetoxyethyl)acrylate (41.44 g) as a colorless oil.

Workup

  1. customquenched with water (200 ml)
  2. customThe aqueous layer was separated
  3. extractionextracted twice with dichloromethane
  4. washThe combined organic layers were washed with 1N hydrochloric acid, saturated aqueous sodium hydrogen carbonate water
  5. dry with materialan aqueous sodium chloride in turn, and then, dried over magnesium sulfate
  6. customAfter the resultant solution was evaporated
  7. distillationthe residue was distilled in vacuo

Sources & evidence

ORD record
ord-914739af950d4b6d8a49190b0be7459a
Source dataset
uspto-grants-1993_08
Patent number
US05241064

Reaction notes

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