Aluminium lithium hydride → (2-Isopropyl-furan-3-yl)-methanol

HRID 490362Notes

Reaction equation

HRID 490362 reaction equation
C([O:3][C:4]([C:6]1[CH:10]=[CH:9][O:8][C:7]=1[CH:11]([CH3:13])[CH3:12])=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH:11]([C:7]1[O:8][CH:9]=[CH:10][C:6]=1[CH2:4][OH:3])([CH3:13])[CH3:12]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 588241892-Isopropyl-furan-3-carboxylic acid ethyl ester

Product 1

HCID 18444637(2-Isopropyl-furan-3-yl)-methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-isopropyl-furan-3-carboxylic acid ethyl ester (82) (4.0 g, 21.95 mmoles) in tetrahydrofuran (70 ml) was treated portionwise during 0.5 h with lithium aluminium hydride (0.7 g, 18.4 mmoles) under a nitrogen atmosphere. When the addition was complete the mixture was stirred at room temperature for 18 hours, then quenched by the addition of excess acetone (1 ml) and then water (1 ml). After diluting with ethyl acetate (150 ml) the grey precipitate was removed by filtration. The filtrate was evaporated and the residue dissolved in diethyl ether and dried. Evaporation of the solvent afforded (2-isopropyl-furan-3-yl)-methanol. 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 (150 ml) the grey precipitate
  4. customwas removed by filtration
  5. customThe filtrate was evaporated
  6. dissolutionthe residue dissolved in diethyl ether
  7. customdried
  8. customEvaporation of the solvent

Sources & evidence

ORD record
ord-c3b8b9ce7ad549da839552ed6345ce6b
Source dataset
uspto-grants-2009_05
Patent number
US07528157B2

Reaction notes

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