Hydrochloric Acid → 3-[2-(4-Bromo-phenyl)-5-methyl-oxazol-4-yl]-propan-1-ol

HRID 1445767Notes

Reaction equation

HRID 1445767 reaction equation
CC(C[AlH]CC(C)C)C.[Br:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[O:18][C:19]([CH3:26])=[C:20]([CH2:22][CH2:23][CH:24]=[O:25])[N:21]=2)=[CH:13][CH:12]=1.Cl>ClCCl>[Br:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]2[O:18][C:19]([CH3:26])=[C:20]([CH2:22][CH2:23][CH2:24][OH:25])[N:21]=2)=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 14487Diisobutylaluminum hydrideHCID 860966863-[2-(4-Bromo-phenyl)-5-methyl-oxazol-4-yl]-propionaldehyde

Product 1

HCID 589514563-[2-(4-Bromo-phenyl)-5-methyl-oxazol-4-yl]-propan-1-olYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add DIBAL-H (1M in THF, 2.0 mL, 2.0 mmol) to a 0° C. solution of 3-[2-(4-bromo-phenyl)-5-methyl-oxazol-4-yl]-propionaldehyde (0.395 g, 1.39 mmol) in dichloromethane. After 15 min add 1N HCl and warm to room temperature. Add 5N HCl and stir until two clear, homogeneous layers are formed. Separate the layers and extract the aqueous layer with dichloromethane. Dry the crude organic extracts over MgSO4, filter, and concentrate. Purify on silica gel (0-70% EtOAc/Hexanes) to give the title compound (0.315 g, 79%): MS (m/e): 296 (M+1).

Workup

  1. customhomogeneous layers are formed
  2. customSeparate the layers
  3. extractionextract the aqueous layer with dichloromethane
  4. dry with materialDry the crude organic extracts over MgSO4
  5. filtrationfilter
  6. concentrationconcentrate
  7. customPurify on silica gel (0-70% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-c81246c074d148eeaef7564c6379e77d
Source dataset
uspto-grants-2010_02
Patent number
US07666871B2

Reaction notes

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