Hydrochloric Acid → HCID 69422309, compound

HRID 349907Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1[O:12][C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:10][C:9]=1[CH2:19][O:20][C:21]1[CH:44]=[CH:43][C:24]([CH2:25][N:26]2[CH:30]=[C:29]([CH2:31][CH2:32][C:33](OC)=[O:34])[C:28]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)=[N:27]2)=[CH:23][CH:22]=1.O.Cl>C(OCC)C>[CH3:7][C:8]1[O:12][C:11]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[N:10][C:9]=1[CH2:19][O:20][C:21]1[CH:44]=[CH:43][C:24]([CH2:25][N:26]2[CH:30]=[C:29]([CH2:31][CH2:32][CH2:33][OH:34])[C:28]([C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)=[N:27]2)=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Lithium aluminium hydride (262 mg) was added to a solution of methyl 3-[1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-3-phenyl-1H-pyrazol-4-yl]propionate (3.50 g) in diethyl ether (50 ml) at 0° C., and the mixture was stirred at 0° C. for one hour. After adding water, the reaction mixture was acidified with diluted hydrochloric acid, which was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), and then concentrated. The residue was subjected to silica gel column chromatography, and 3-[1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-3-phenyl-1H-pyrazol-4-yl]propan-1-ol (3.04 g, yield: 92%) was obtained as a colorless oily substance from the fraction eluted with ethyl acetate-hexane (3:2, volume ratio).

Workup

extractionwas extracted with ethyl acetate
washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
dry with materialdried (MgSO4)
concentrationconcentrated

Sources & evidence

ORD record: ord-e8e1e4aa9d25474891ffff17a8a37849
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07179823B1

Reaction notes

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