Hydrochloric Acid → (E)-3-[3-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]-2-propenol

HRID 1739031Notes

Reaction equation

HRID 1739031 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[CH3:11][C:12]1[O:16][C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:14][C:13]=1[CH2:23][O:24][C:25]1[CH:26]=[C:27]([CH:35]=[CH:36][CH:37]=1)[CH:28]=[CH:29][C:30](OCC)=[O:31].Cl>C1(C)C=CC=CC=1.ClCCl>[CH3:11][C:12]1[O:16][C:15]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[N:14][C:13]=1[CH2:23][O:24][C:25]1[CH:26]=[C:27](/[CH:28]=[CH:29]/[CH2:30][OH:31])[CH:35]=[CH:36][CH:37]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 21225700DiisobutylaluminumhydrideHCID 53825120Ethyl 3-(5-methyl-2-phenyl-4-oxazolylmethoxy)cinnamate

Product 1

HCID 10860209(E)-3-[3-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]-2-propenolYield 92.9%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of diisobutyl aluminum hydride in toluene (1.5M, 51 ml) was added dropwise to a solution of ethyl 3-(5-methyl-2-phenyl-4-oxazolylmethoxy)cinnamate (14.0 g) in dichloromethane (200 ml) at 0° C. After stirring for 30 minutes, 2N hydrochloric acid (150 ml) was added at 0° C., and the mixture was stirred for 1 hour. The dichloromethane layer was separated, washed with saturated brine and dried over magnesium sulfate. Evaporation of the solvent under reduced pressure gave crystals of (E)-3-[3-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]-2-propenol (11.5 g, 92%). The crystals were recrystallized from ethyl acetate. Colorless prisms, mp: 118-119° C.

Workup

  1. stirringthe mixture was stirred for 1 hour
  2. customThe dichloromethane layer was separated
  3. washwashed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. customEvaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-3e2f8296dc1d4db5b4f9df120ff52962
Source dataset
uspto-grants-1999_10
Patent number
US05965589

Reaction notes

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