5-(1-Hydroxy-ethyl)-2-methyl-furan-3-carboxylic acid methyl ester → Methyl 5-acetyl-2-methylfuran-3-carboxylate

HRID 68574Notes

Reaction equation

HRID 68574 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:9]=[C:8]([CH:10]([OH:12])[CH3:11])[O:7][C:6]=1[CH3:13])=[O:4]>ClCCl.[O-2].[O-2].[Mn+4]>[CH3:1][O:2][C:3]([C:5]1[CH:9]=[C:8]([C:10](=[O:12])[CH3:11])[O:7][C:6]=1[CH3:13])=[O:4]

Participants

4

Reactant 1

HCID 682926955-(1-Hydroxy-ethyl)-2-methyl-furan-3-carboxylic acid methyl ester

Product 1

HCID 10866962Methyl 5-acetyl-2-methylfuran-3-carboxylateYield 83.5%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

Manganese dioxide (669 g) is added portionwise to a solution of 5-(1-hydroxy-ethyl)-2-methyl-furan-3-carboxylic acid methyl ester (94.5 g) in dichloromethane (1000 ml). After 72 hours at room temperature, the reaction mixture is filtered through a plug of silica gel and the filtration cake is washed several times with ethyl acetate. The filtrate is concentrated in verve to yield 5-acetyl-2-methyl-furan-3-carboxylic acid methyl ester (78 g) as a yellow solid. The crude product obtained is used without further purification. MS (HPLC/MS): 183 (MH+).

Workup

  1. filtrationthe reaction mixture is filtered through a plug of silica gel
  2. washthe filtration cake is washed several times with ethyl acetate
  3. concentrationThe filtrate is concentrated in verve

Sources & evidence

ORD record
ord-aafebca82d60446fb357fa4ebbcb95d5
Source dataset
uspto-grants-2014_09
Patent number
US08822466B2

Reaction notes

Loading…