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

HRID 1528834Notes

Reaction equation

HRID 1528834 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

Procedure

To 1-(4-bromo-phenyl)-cyclopropanecarboxylic acid ethyl ester (10.0 g, 37.2 mmol) in THF (100 mL) at 0° C. was added lithium aluminum hydride (2.11 g, 55.7 mmol) and the reaction was stirred for 1 hour at room temperature. The mixture was quenched with H2O (2 mL), followed by 4 N aqueous NaOH (2 mL) and additional H2O (6 mL). After stirring for 15 minutes, the solid precipitate was removed by filtration and the filtrate was concentrated and dried to give the title compound.

Workup

  1. customThe mixture was quenched with H2O (2 mL)
  2. stirringAfter stirring for 15 minutes
  3. customthe solid precipitate was removed by filtration
  4. concentrationthe filtrate was concentrated
  5. customdried

Sources & evidence

ORD record
ord-7ac50cbef6494b6b8fe5bb383f4cff32
Source dataset
uspto-grants-2015_07
Patent number
US09090573B2

Reaction notes

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