Methyl Acrylate → Methyl 3-(furan-2-yl)prop-2-enoate

HRID 444122Notes

Reaction equation

HRID 444122 reaction equation
[C:1]([O:5][CH3:6])(=[O:4])[CH:2]=[CH2:3].[C]=O.[O:9]1[CH:13]=[CH:12][CH:11]=[CH:10]1>>[O:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[CH:3]=[CH:2][C:1]([O:5][CH3:6])=[O:4]

Participants

4

Reactant 3

HCID 7294Methyl AcrylateHCID 8029FuranHCID 178418416HCID 178418416, compound

Product 1

HCID 61165Methyl 3-(furan-2-yl)prop-2-enoateYield 39%

Procedure

Charged in a shaking type stainless steel autoclave having an inner capacity of 100 ml, were 30 ml of furan, 1.083 g of methyl acrylate and 0.04 g of Rh4 (CO)12, followed by supply of carbon monoxide under 25 kg/cm2. Reaction was carried out at 220° C. for 7 hours. After completion of the reaction, the obtained reddish orange reaction solution was concentrated under reduced pressure and separated and purified by silica gel column chromatography. From a fraction eluted with benzene/hexane (3/2 to 4/1) was obtained 0.74 g of methyl β-(2-furyl)acrylate (1) (the yield was 39% based on methyl acrylate).

Workup

  1. customReaction
  2. customAfter completion of the reaction
  3. concentrationthe obtained reddish orange reaction solution was concentrated under reduced pressure
  4. customseparated
  5. custompurified by silica gel column chromatography
  6. washFrom a fraction eluted with benzene/hexane (3/2 to 4/1)

Sources & evidence

ORD record
ord-2aaedb10102e4f4a98c6ffbfef293fa2
Source dataset
uspto-grants-1981_04
Patent number
US04263212

Reaction notes

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