HCID 66819893, compound → 1-(5-hydroxymethyl-furan-2-yl)-ethanone

HRID 2040045Notes

Reaction equation

HRID 2040045 reaction equation
O1CCCCC1[O:7][CH2:8][C:9]1[O:13][C:12]([C:14](=[O:16])[CH3:15])=[CH:11][CH:10]=1>CO>[OH:7][CH2:8][C:9]1[O:13][C:12]([C:14](=[O:16])[CH3:15])=[CH:11][CH:10]=1

Participants

3

Reactant 1

HCID 66819893HCID 66819893, compound

Product 1

HCID 5803811-(5-hydroxymethyl-furan-2-yl)-ethanoneYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
35 °C

Procedure

Crude 1-[5-(tetrahydro-pyran-2-yloxymethyl)-furan-2-yl]-ethanone (89 g, 0.40 mol) was dissolved in MeOH (500 mL) and treated with Amberlyst 15 (15 g) at rt. The reaction mixture was stirred at 35° C. for 1 h, cooled to rt and filtered over celite. Et3N (1 mL) was added and the mixture was evaporated to dryness. The residue was stripped with methylcyclohexane and 1-(5-hydroxymethyl-furan-2-yl)-ethanone (55 g, 99%) was obtained as a yellow oil that solidified on standing.

Workup

  1. temperaturecooled to rt
  2. filtrationfiltered over celite
  3. additionEt3N (1 mL) was added
  4. customthe mixture was evaporated to dryness

Sources & evidence

ORD record
ord-9e1f1aa9853443f58b1b2fead314e3fc
Source dataset
uspto-grants-2013_11
Patent number
US08580831B2

Reaction notes

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