Water → 2-(5-Methyl-2-phenyl-4-oxazolyl)ethanol

HRID 4401

Reaction equation

HRID 4401 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][C:14](OC)=[O:15].[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C.O>C(OCC)C>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][OH:15]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 2775318Methyl (5-methyl-2-phenyl-1,3-oxazol-4-yl)acetateHCID 21226445Aluminium lithium hydride

Product 1

HCID 7255852-(5-Methyl-2-phenyl-4-oxazolyl)ethanolYield 96.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of methyl 5-methyl-2-phenyl-4-oxazoleacetate (54 g) in dry ethyl ether (150 ml) was added dropwise to a stirred, ice-cooled suspension of lithium aluminum hydride (8.8 g) in dry ethyl ether (700 ml) during 1.5 hours. Ethyl acetate (20 ml) was added dropwise thereto with ice-cooling and then water (50 ml) was added cautiously thereto. The resulting white precipitate was filtered off and the filtrate was concentrated to give 2-(5-methyl-2-phenyl-4-oxazolyl) ethanol as crystals (45.8 g, 96.2%). Recrystallization from ethyl acetate-hexane gave colorless rods, m.p. 73°-74° C.

Workup

  1. temperaturecooled
  2. temperaturewith ice-cooling
  3. filtrationThe resulting white precipitate was filtered off
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-55ea6960f61b4354bc71a258ea910ffe
Source dataset
uspto-grants-1988_02
Patent number
US04725610

Linked notes

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