Aluminium lithium hydride → [2-(4-Bromo-phenyl)4-isopropyl-oxazol-5-yl]-methanol

HRID 860591Notes

Reaction equation

HRID 860591 reaction equation
C([O:3][C:4]([C:6]1[O:10][C:9]([C:11]2[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][CH:12]=2)=[N:8][C:7]=1[CH:18]([CH3:20])[CH3:19])=O)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[Br:17][C:14]1[CH:13]=[CH:12][C:11]([C:9]2[O:10][C:6]([CH2:4][OH:3])=[C:7]([CH:18]([CH3:20])[CH3:19])[N:8]=2)=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 690532562-(4-Bromo-phenyl)4-isopropyl-oxazole-5-carboxylic acid ethyl ester

Product 1

HCID 69056838[2-(4-Bromo-phenyl)4-isopropyl-oxazol-5-yl]-methanolYield 99.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(4-bromo-phenyl)-4-isopropyl-oxazole-5-carboxylic acid ethyl ester (20.6 g, 60.9 mmol) in THF (300 mL) is cooled in an ice-water bath and treated portionwise with LiAlH4 (2.8 g, 73 mmol). The reaction is complete after 1.5 h. Ice chips (˜10 g) are added to quench the excess hydride reagent, and anhydrous Na2SO4 (˜50 g) is added. The thick suspension is stirred 30 min, filtered through celite, and washed with THF (600 mL). The filtrate is dried (Na2SO4) and concentrated. The crude product is purified by silica gel flash chromatography using hexanes:ethyl acetate (3:1) to give a white solid (17.9 g, 99%).

Workup

  1. additionIce chips (˜10 g) are added
  2. customto quench the excess hydride reagent, and anhydrous Na2SO4 (˜50 g)
  3. additionis added
  4. filtrationfiltered through celite
  5. washwashed with THF (600 mL)
  6. dry with materialThe filtrate is dried (Na2SO4)
  7. concentrationconcentrated
  8. customThe crude product is purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-3164cb9d47df4711a0ab760165664d8c
Source dataset
uspto-grants-2006_12
Patent number
US07153878B2

Reaction notes

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