Water → HCID 23361347, compound

HRID 233292Notes

Reaction equation

HRID 233292 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][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH2:23][CH2:24][C:25](OCC)=[O:26])=[CH:17][CH:16]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>CCOCC>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][OH:26])=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 23361382HCID 23361382, compound

Product 1

HCID 23361347HCID 23361347, compoundYield 94.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of ethyl 5-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]valerate (2.55 g) in ether (20 ml) was added dropwise, under ice-cooling, to a suspension of lithium aluminum hydride (LiAlH4) (0.247 g) in ether (40 ml). The mixture was stirred for 15 minutes under ice-cooling, to which was added water (2 ml). Insoluble solid was filtered off, and the filtrate was concentrated to give 5-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]-1-pentanol (2.15 g, 94%), which was recrystallized from ethyl acetate--hexane to give colorless rods, m.p.78°-79° C.

Workup

  1. temperaturecooling, to which
  2. filtrationInsoluble solid was filtered off
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-e36a65ef9af34062b86d8565261aa658
Source dataset
uspto-grants-1997_01
Patent number
US05591862

Reaction notes

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