Aluminium lithium hydride → HCID 15936950, compound

HRID 1280740Notes

Reaction equation

HRID 1280740 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C[O:8][C:9](=O)[CH:10]([F:19])[CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1COCC1>[F:19][CH:10]([CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:9][OH:8]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86584023HCID 86584023, compound

Product 1

HCID 15936950HCID 15936950, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a 0° C. suspension of LiAlH4 (0.4 g, 10.6 mmol) in dry THF (5 ml) was added dropwise a solution of (RS)-2-fluoro-4-phenyl-butyric acid methyl ester (1 g, 5.3 mmol) in dry THF (10 ml). After 1 hour stirring at 0° C., the reaction mixture was quenched successively with H2O (0.4 ml), 5N NaOH (0.4 ml) and again H2O (1.2 ml). The resulting solid was filtered and the filtrate was concentrated to provide (RS)-2-fluoro-4-phenyl-butan-1-ol (0.89 g, 99%) as a colorless oil, MS: m/e=168.1 (M+).

Workup

  1. customthe reaction mixture was quenched successively with H2O (0.4 ml), 5N NaOH (0.4 ml) and again H2O (1.2 ml)
  2. filtrationThe resulting solid was filtered
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-9efcf73044344bba87983126c711ab7b
Source dataset
uspto-grants-2002_09
Patent number
US06451819B2

Reaction notes

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