Aluminium lithium hydride → 2-Methyl-5-(trifluoromethyl)-3-furanmethanol

HRID 591526Notes

Reaction equation

HRID 591526 reaction equation
[CH3:1][C:2]1[O:3][C:4]([C:12]([F:15])([F:14])[F:13])=[CH:5][C:6]=1[C:7](OCC)=[O:8].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH3:1][C:2]1[O:3][C:4]([C:12]([F:14])([F:13])[F:15])=[CH:5][C:6]=1[CH2:7][OH:8]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 89767734HCID 89767734, compound

Product 1

HCID 897681052-Methyl-5-(trifluoromethyl)-3-furanmethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of ethyl 2-methyl-5-(trifluoromethyl)furan-3-carboxylate (720 mg) and THF (dry) (10 mL) was added lithium aluminum hydride (123 mg) at 0° C., and the mixture was stirred for 3 h. The mixture was quenched with EtOAc at 0° C. and 1N HCl was added to the mixture at same temperature. The organic layer was separated, washed successively with 1N HCl and brine, dried over MgSO4 and concentrated in vacuo to give title compound.

Workup

  1. customThe mixture was quenched with EtOAc at 0° C.
  2. addition1N HCl was added to the mixture at same temperature
  3. customThe organic layer was separated
  4. washwashed successively with 1N HCl and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ebc1e88dbc8840898fde03996c3065e0
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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