Water → [2-(4-Chloro-3-methylphenyl)-1,3-oxazol-4-yl]methanol

HRID 508158Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[O:15][CH:16]=[C:17]([C:19](OCC)=[O:20])[N:18]=2)=[CH:10][C:9]=1[CH3:24].O.[OH-].[Na+]>C1COCC1>[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[O:15][CH:16]=[C:17]([CH2:19][OH:20])[N:18]=2)=[CH:10][C:9]=1[CH3:24]

Participants

Conditions

Temperature: 0 °C

Procedure

46 mg (1.22 mmol) of lithium aluminum hydride are initially charged in 8.0 ml of THF and cooled to 0° C. A solution of 161 mg (0.61 mmol) of the compound from Example 26A in 2.5 ml of THF is then added dropwise. The mixture is stirred at RT for 2 h. The reaction solution is then once more cooled to 0° C., and 0.2 ml of water and 0.4 ml of 1 N aqueous sodium hydroxide solution are added. The mixture is stirred at RT overnight. The precipitate formed is filtered off, and the filtrate is freed from the solvent using a rotary evaporator. The residue is used without further purification in the subsequent reaction.

Workup

temperatureThe reaction solution is then once more cooled to 0° C.
stirringThe mixture is stirred at RT overnight
customThe precipitate formed
filtrationis filtered off
customa rotary evaporator
customThe residue is used without further purification in the subsequent reaction

Sources & evidence

ORD record: ord-1416c1ca9a0c43d886b805592fc7c512
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09095582B2

Reaction notes

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