2-(tert-Butyl(dimethyl)silyl)oxyethanol → 1-(2-(2-((tert-butyldimethylsilyl)oxy)ethoxy)-5-nitrophenyl)-4-methyl-1,4-dihydro-5H-tetrazol-5-one

HRID 633441Notes

Reaction equation

HRID 633441 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[N:11]1[C:15](=[O:16])[N:14]([CH3:17])[N:13]=[N:12]1.CC(C)([O-])C.[K+].[Si:24]([O:31][CH2:32][CH2:33][OH:34])([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25]>C1COCC1>[Si:24]([O:31][CH2:32][CH2:33][O:34][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[N:11]1[C:15](=[O:16])[N:14]([CH3:17])[N:13]=[N:12]1)([C:27]([CH3:29])([CH3:30])[CH3:28])([CH3:26])[CH3:25]

Participants

5

Reactant 3

HCID 111376652-(tert-Butyl(dimethyl)silyl)oxyethanolHCID 23665647Potassium tert-butoxideHCID 582871741-(2-fluoro-5-nitrophenyl)-4-methyl-1H-tetrazol-5(4H)-one

Product 1

HCID 867045331-(2-(2-((tert-butyldimethylsilyl)oxy)ethoxy)-5-nitrophenyl)-4-methyl-1,4-dihydro-5H-tetrazol-5-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A similar procedure as detailed below for Compound 133 was used. 1-(2-fluoro-5-nitrophenyl)-4-methyl-1,4-dihydro-5H-tetrazol-5-one (prepared according to US patent application no. 2011/0130415) (250 mg, 1.1 mmol), potassium tert-butoxide (258 mg, 2.3 mmol) and 2-((tert-butyldimethylsilyl)oxy)ethan-1-ol (369 mg, 2.1 mmol) in THF (2 mL) was stirred for 1 hr at room temperature to give the product after workup (yield assumed quantitative=413 mg). The product was used in the next step without further purification.

Workup

  1. customto give the product
  2. customafter workup (yield assumed quantitative=413 mg)
  3. customThe product was used in the next step without further purification

Sources & evidence

ORD record
ord-fb325f1bc1dd4749bdef96e574387409
Source dataset
uspto-grants-2016_04
Patent number
US09321763B2

Reaction notes

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