Aluminium lithium hydride → HCID 53275778, compound

HRID 889021Notes

Reaction equation

HRID 889021 reaction equation
C([O:3][C:4]([CH:6]1[CH2:8][CH:7]1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[F:16][C:15]([F:17])([F:18])[C:11]1[CH:10]=[C:9]([CH:7]2[CH2:8][CH:6]2[CH2:4][OH:3])[CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 574296592-(3-Trifluoromethyl-phenyl)-cyclopropanecarboxylic acid ethyl ester

Product 1

HCID 53275778HCID 53275778, compoundYield 92.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
22.5 °C

Procedure

2-(3-Trifluoromethyl-phenyl)-cyclopropanecarboxylic acid ethyl ester (prepared as per literature procedure) (0.70 g, 2.7 mmol) in THF (5 ml) was added to a solution of lithium aluminium hydride (0.123 g, 3.25 mmol) in THF (5 ml) at 0° C. over a period of 10 min. and stirred further at 20-25° C. for 2 hours. The reaction mixture was diluted with THF (15 ml) and quenched with 10% NaOH solution (5 ml) and water (10 ml). The aqueous layer was extracted with ethyl acetate, washed with saturated brine solution and dried over Na2SO4. The organic layer was evaporated to afford [2-(3-trifluoromethyl-phenyl)-cyclopropyl]-methanol as a colorless oil (0.54 g, 92%).

Workup

  1. customquenched with 10% NaOH solution (5 ml) and water (10 ml)
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. washwashed with saturated brine solution
  4. dry with materialdried over Na2SO4
  5. customThe organic layer was evaporated

Sources & evidence

ORD record
ord-503da88fceca4934aee6d04ca9cbcd49
Source dataset
uspto-grants-2012_08
Patent number
US08252797B2

Reaction notes

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