Ethyl 2-(trifluoromethyl)furan-3-carboxylate → (2-Trifluoromethyl-furan-3-yl)-methanol

HRID 490363Notes

Reaction equation

HRID 490363 reaction equation
C([O:3][C:4]([C:6]1[CH:10]=[CH:9][O:8][C:7]=1[C:11]([F:14])([F:13])[F:12])=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[F:14][C:11]([F:12])([F:13])[C:7]1[O:8][CH:9]=[CH:10][C:6]=1[CH2:4][OH:3]

Participants

4

Reactant 2

HCID 4737733Ethyl 2-(trifluoromethyl)furan-3-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 17953606(2-Trifluoromethyl-furan-3-yl)-methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-trifluoromethyl-furan-3-carboxylic acid ethyl ester (2.2 g, 10.5 mmoles) in tetrahydrofuran (150 ml) was treated portionwise during 0.5 h with lithium aluminium hydride (0.55 g, 14.5 mmoles) under a nitrogen atmosphere. When the addition was complete the mixture was stirred at room temperature for 18 h, then quenched by the addition of excess acetone (1 ml) and then water (1 ml). After diluting with ethyl acetate (200 ml) the grey precipitate was removed by filtration. The filtrate was dried and evaporation of the solvent afforded (2-trifluoromethyl-furan-3-yl)-methanol as a colourless oil. This material was used immediately in the next step.

Workup

  1. additionWhen the addition
  2. customquenched by the addition of excess acetone (1 ml)
  3. additionAfter diluting with ethyl acetate (200 ml) the grey precipitate
  4. customwas removed by filtration
  5. customThe filtrate was dried
  6. customevaporation of the solvent

Sources & evidence

ORD record
ord-da52f3e8f88c40a48b32acb4d468c3c3
Source dataset
uspto-grants-2009_05
Patent number
US07528157B2

Reaction notes

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