Water → HCID 19744637, compound

HRID 2254460Notes

Reaction equation

HRID 2254460 reaction equation
[O:1]1[C:5]([C:6](OC)=[O:7])=[CH:4][C:3]([C:10]([O:12][CH3:13])=[O:11])=[CH:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.C(OCC)(=O)C>O1CCCC1>[OH:7][CH2:6][C:5]1[O:1][CH:2]=[C:3]([C:10]([O:12][CH3:13])=[O:11])[CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 592845HCID 592845, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19744637HCID 19744637, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

408 mg of dimethyl furan-3,5-dicarboxylate [see J. Chem. Soc., Perkin I, 1130 (1973)] was dissolved in 4 ml of anhydrous tetrahydrofuran, and 59 mg of lithium aluminium hydride was added. The mixture was stirred overnight at room temperature. The reaction mixture was poured into water, and ethyl acetate was added to extract it. The extract was worked up in a customary manner and purified by silica gel column chromatography [Wakogel C-200, 20 g; eluting solvent: hexane/ethyl acetate=2/1] to give 44 mg (yield 13%) of methyl 5-hydroxymethylfuran-3-carboxylate as a colorless oil.

Workup

  1. additionwas added
  2. extractionto extract it
  3. custompurified by silica gel column chromatography [Wakogel C-200, 20 g; eluting solvent: hexane/ethyl acetate=2/1]

Sources & evidence

ORD record
ord-8a525f43da584e68a137874171ab3ccd
Source dataset
uspto-grants-1993_08
Patent number
US05234946

Reaction notes

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