Methyl Acrylate → HCID 54430997, compound

HRID 444124Notes

Reaction equation

HRID 444124 reaction equation
[C:1]([C:4]1[O:5][CH:6]=[CH:7][CH:8]=1)(=[O:3])[CH3:2].[C:9]([O:13][CH3:14])(=[O:12])[CH:10]=[CH2:11].[C]=O>O1CCCC1>[C:1]([C:4]1[O:5][C:6]([CH:11]=[CH:10][C:9]([O:13][CH3:14])=[O:12])=[CH:7][CH:8]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7294Methyl AcrylateHCID 145052-AcetylfuranHCID 178418416HCID 178418416, compound

Product 1

HCID 54430997HCID 54430997, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Charged in a stainless steel autoclave having an inner capacity of 200 ml were 5.5 g of 2-acetylfuran, 1.72 g of methyl acrylate, 0.038 g of Rh4 (CO)12 and 50 ml of tetrahydrofuran, followed by supply of carbon monoxide under 30 kg/cm2. Reaction was carried out at 220° C. for 7 hours. Tetrahydrofuran and unreacted 2-acetylfuran were removed from the obtained light brown solution by distillation under reduced pressure, and the residue was separated and purified by silica gel column chromatography. From a fraction eluted with methylene chloride was obtained 0.62 g of methyl β-(5-acetyl-2-furyl)acrylate (3) (the yield was 16%).

Workup

  1. customReaction
  2. customTetrahydrofuran and unreacted 2-acetylfuran were removed from the obtained light brown solution by distillation under reduced pressure
  3. customthe residue was separated
  4. custompurified by silica gel column chromatography
  5. washFrom a fraction eluted with methylene chloride

Sources & evidence

ORD record
ord-e71b24078b624888a3afe9a21e47539d
Source dataset
uspto-grants-1981_04
Patent number
US04263212

Reaction notes

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