Water → [5-(4-Fluoro-phenyl)-3-trimethylsilanylmethyl-3H-[1,2,3]triazol-4-yl]-methanol

HRID 402353Notes

Reaction equation

C([O:3][C:4]([C:6]1[N:7]([CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[N:8]=[N:9][C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1>[F:17][C:14]1[CH:15]=[CH:16][C:11]([C:10]2[N:9]=[N:8][N:7]([CH2:18][Si:19]([CH3:20])([CH3:21])[CH3:22])[C:6]=2[CH2:4][OH:3])=[CH:12][CH:13]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 5-(4-fluoro-phenyl)-3-trimethylsilanylmethyl-3H-[1,2,3]triazole-4-carboxylic acid ethyl ester (880 mg, 2.74 mmol) in dry THF (8.2 mL) was added portionwise lithiumaluminiumhydride (119 mg, 3.15 mmol) at 0° C. and the reaction mixture was stirred at 0° C. for 1 h. Then water (119 μL) and NaOH (15%, 119 μL) was added followed by water (357 μL). The precipitate was then filtered off and the filtrate evaporated. Purification by chromatography (silica, 0 to 100% ethyl acetate in heptane) afforded the title compound (649 mg, 85%) as a white solid. MS: m/e=280.1 [M+H]+.

Workup

filtrationThe precipitate was then filtered off
customthe filtrate evaporated
customPurification by chromatography (silica, 0 to 100% ethyl acetate in heptane)

Sources & evidence

ORD record: ord-1782d90abd8245bebe1b5b3b457b9aae
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08742097B2

Reaction notes

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