Aluminium lithium hydride → (1-(4-Bromophenyl)cyclopropyl)methanol

HRID 1183325Notes

Reaction equation

HRID 1183325 reaction equation
C([O:3][C:4]([C:6]1([C:9]2[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][CH:10]=2)[CH2:8][CH2:7]1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[Br:15][C:12]1[CH:11]=[CH:10][C:9]([C:6]2([CH2:4][OH:3])[CH2:7][CH2:8]2)=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 53216840Ethyl 1-(4-bromophenyl)cyclopropanecarboxylate

Product 1

HCID 20252945(1-(4-Bromophenyl)cyclopropyl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-4 °C

Procedure

1-(4-Bromo-phenyl)-cyclopropanecarboxylic acid ethyl ester (25 g, 92.89 mmol) was dissolved in THF (175 mL) and was stirred under N2 atmosphere at −4° C. Lithium aluminum hydride (4.58 g, 120.75 mmol) was added in portions and the reaction stirred between 2 to 8° C. for 1 hour. The reaction was worked up using the Fieser method, filtered and concentrated to afford the title compound.

Workup

  1. stirringthe reaction stirred between 2 to 8° C. for 1 hour
  2. filtrationfiltered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-fecfc81d224145bf9ae1a2c6fca16322
Source dataset
uspto-grants-2014_03
Patent number
US08664220B2

Reaction notes

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