Water → 3-[1-(triphenylmethyl)-1H-1,2,4-triazol-3-yl]propan-1-ol

HRID 606457Notes

Reaction equation

[C:1]1([C:7]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:8]2[CH:12]=[N:11][C:10]([CH2:13][CH2:14][C:15](OCC)=[O:16])=[N:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1>[C:26]1([C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:8]2[CH:12]=[N:11][C:10]([CH2:13][CH2:14][CH2:15][OH:16])=[N:9]2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of ethyl 3-[1-(triphenylmethyl)-1H-1,2,4-triazol-3-yl]propanoate obtained in Reference Example 24 (700 mg, 1.70 mmol) in THF (5 mL) was added to a suspension of lithium aluminum hydride (84.0 mg, 2.21 mmol) in THF (5 mL) at 0° C., and the mixture was stirred at 0° C. for 5 hr, and then at room temperature for 15 hr. Water and 1N aqueous sodium hydroxide solution were added to the mixture, and the insoluble material was filtered off. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (0-80% ethyl acetate/hexane) to give the title compound as a white powder (289 mg, 46%).

Workup

waitat room temperature for 15 hr
filtrationthe insoluble material was filtered off
concentrationThe filtrate was concentrated under reduced pressure
customthe residue was purified by silica gel column chromatography (0-80% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-c3d1591e725e4b6683d85e67debe58be
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07915267B2

Reaction notes

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