Aluminium lithium hydride → 3-(2-Chloro-6-fluorophenyl)propan-1-ol

HRID 408488Notes

Reaction equation

HRID 408488 reaction equation
C([O:3][C:4](=O)[CH:5]=[CH:6][C:7]1[C:12]([F:13])=[CH:11][CH:10]=[CH:9][C:8]=1[Cl:14])C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[Cl:14][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]([F:13])[C:7]=1[CH2:6][CH2:5][CH2:4][OH:3]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 67314943HCID 67314943, compound

Product 1

HCID 282970863-(2-Chloro-6-fluorophenyl)propan-1-olYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 3-(2-chloro-6-fluoro-phenyl)-acrylic acid ethyl ester in dried tetrahydrofuran (300 mL) was added to a suspension of lithium aluminum hydride (30 g, 0.78 mol) in anhydrous tetrahydrofuran (200 mL) at 0° C. The reaction mixture was stirred for 3 hours, and then cooled to 0° C. and quenched by the addition of water (30 g) and a 10% aqueous solution of sodium hydroxide (30 mL). The resulting solid was filtered, washed with tetrahydrofuran, and then purified by silica gel column chromatography to afford 3-(2-chloro-6-fluoro-phenyl)-propan-1-ol (21 g, 0.11 mol, 43% from 2-chloro-6-fluoro-benzaldehyde).

Workup

  1. customquenched by the addition of water (30 g)
  2. filtrationThe resulting solid was filtered
  3. washwashed with tetrahydrofuran
  4. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-0a123db153e94bf1a78558d320a4f2cc
Source dataset
uspto-grants-2014_06
Patent number
US08759335B2

Reaction notes

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