Water → HCID 20279269, compound

HRID 2166706Notes

Reaction equation

HRID 2166706 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9].[CH:13](OCC)=[O:14].[H-].[Na+].O>C(COC)OC>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH:7]([CH:13]=[O:14])[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

6

Reactant 4

HCID 962WaterHCID 8025Ethyl formateHCID 24758Sodium hydrideHCID 61450Ethyl 2-furanpropionate

Product 1

HCID 20279269HCID 20279269, compoundYield 48.2%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of ethyl 3-(2-furanyl)propionate (33.77 g) and ethyl formate (22.22 g) was added dropwise with stirring to a pre-cooled (0° C.) suspension of sodium hydride (50% in oil; 8.45 g) in dimethoxyethane (70 ml) maintaining the temperature below 0° C. throughout the addition. The reaction mixture was allowed to warm to room temperature then poured on to ice and water and extracted with ethyl acetate. The aqueous layer was acidified to pH 4 and re-extracted with ethyl acetate. These second ethyl acetate extracts were combined dried (MgSO4) and evaporated at reduced pressure to yield ethyl 3-(2-furanyl)-2-formylpropionate (19.0 g).

Workup

  1. additionwas added dropwise
  2. temperaturea pre-cooled
  3. temperaturemaintaining the temperature below 0° C.
  4. additionthroughout the addition
  5. extractionextracted with ethyl acetate
  6. extractionre-extracted with ethyl acetate
  7. dry with materialThese second ethyl acetate extracts were combined dried (MgSO4)
  8. customevaporated at reduced pressure

Sources & evidence

ORD record
ord-30176c81b2614a8c85498bae2906816c
Source dataset
uspto-grants-1983_06
Patent number
US04388317

Reaction notes

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