Methyl 4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]benzoate → 4-(5-Methyl-2-phenyl-4-oxazolylmethoxy)benzyl alcohol

HRID 644005

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9](=O)[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]2[N:19]=[C:20]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[O:21][C:22]=2[CH3:23])=[CH:12][CH:11]=1>C1COCC1>[CH3:23][C:22]1[O:21][C:20]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[N:19][C:18]=1[CH2:17][O:16][C:13]1[CH:12]=[CH:11][C:10]([CH2:9][OH:8])=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Lithium aluminum hydride (15.5 mL of a 1.0 M solution in THF) is added slowly to a cooled (ice-water bath) solution of the title B compound, 4-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-benzoic acid methyl ester (2.0 g, 6.18 mmol) in THF (30 mL). The mixture is stirred at 0° C. for 3 h, then quenched with saturated sodium bicarbonate, and extracted with EtOAc. The organic solution is washed with brine, dried over magnesium sulfate, and concentrated under vacuum to give the crude product. The product is purified by silica gel chromatography using 30% EtOAc in hexane as the eluent to give [4-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-phenyl]-methanol as a white solid.

Workup

customquenched with saturated sodium bicarbonate
extractionextracted with EtOAc
washThe organic solution is washed with brine
dry with materialdried over magnesium sulfate
concentrationconcentrated under vacuum
customto give the crude product
customThe product is purified by silica gel chromatography

Sources & evidence

ORD record: ord-b3bd0b1ad8524663a3d75ea4da848814
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07700637B2

Linked notes

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