Ethyl Acetate → {6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}methanol

HRID 1258586Notes

Reaction equation

HRID 1258586 reaction equation
[CH3:1][N:2]1[C:6]([C:7](=[N:14][O:15][CH2:16][C:17]2[N:22]=[C:21]([CH:23]=[O:24])[CH:20]=[CH:19][CH:18]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:5][N:4]=[N:3]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+].CCOC(C)=O>C1COCC1>[CH3:1][N:2]1[C:6]([C:7](=[N:14][O:15][CH2:16][C:17]2[N:22]=[C:21]([CH2:23][OH:24])[CH:20]=[CH:19][CH:18]=2)[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[N:5][N:4]=[N:3]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 866531376-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridine-2-carbaldehyde

Product 1

HCID 86653139{6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}methanolYield 49.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridine-2-carbaldehyde (0.4 g, 1.24 mmol, 1 eq.) in 100 ml of dry THF, was added sodium triacetoxyborohydride (0.276 mmol, 1.3 mmol, 1.05 eq.) in one portion. The reaction was stirred for 20 hrs, before the addition of 1M aqueous NaOH (100 ml). The mixture was stirred for 15 mins before extraction with EtOAc. The organic phase was dried over MgSO4 and evaporated. The residue was purified by chromatography on silica gel to give {6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}methanol (0.2 g, 47% yield) as a colourless gum.

Workup

  1. dry with materialThe organic phase was dried over MgSO4
  2. customevaporated
  3. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-1b5cd350fead44c1a1ecf9dcf35f7744
Source dataset
uspto-grants-2013_06
Patent number
US08466176B2

Reaction notes

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