Sodium Hydroxide → [5-(5-Fluoro-pyridin-2-yl)-3-trimethylsilanylmethyl-3H-[1,2,3]triazol-4-yl]-methanol

HRID 402386Notes

Reaction equation

HRID 402386 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][N:12]=1)=O)C.[OH-].[Na+]>C1(C)C=CC=CC=1>[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])=[N:12][CH:13]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 674987655-(5-fluoro-pyridin-2-yl)-3-trimethylsilanylmethyl-3H-[1,2,3]triazole-4-carboxylic acid ethyl ester

Product 1

HCID 67499018[5-(5-Fluoro-pyridin-2-yl)-3-trimethylsilanylmethyl-3H-[1,2,3]triazol-4-yl]-methanolYield 95.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 5-(5-fluoro-pyridin-2-yl)-3-trimethylsilanylmethyl-3H-[1,2,3]triazole-4-carboxylic acid ethyl ester (530 mg, 1.64 mmol) in toluene (15 mL) at −7° C. was added sodiumdihydro-bis(2-methoxyethoxy)aluminate (705 μL, 2.47 mmol) and the reaction mixture was stirred at room temperature for 16 h. The mixture was then cooled with ice and NaOH (1 N, 3.3 mL) and extracted with ethyl acetate and the combined organic extracts washed with brine, dried over sodium sulphate, filtered and evaporated to afford the title compound (440 mg, 84%) as a light brown oil. MS: m/e=281.1 [M+H]+.

Workup

  1. extractionextracted with ethyl acetate
  2. washthe combined organic extracts washed with brine
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-357e1252268f492089a98f40d627be48
Source dataset
uspto-grants-2014_06
Patent number
US08742097B2

Reaction notes

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