Methanol → HCID 18406849, compound

HRID 1383834Notes

Reaction equation

HRID 1383834 reaction equation
[Si]([O:8][CH2:9][C:10]1[N:14]([CH2:15][CH2:16][CH3:17])[N:13]=[CH:12][N:11]=1)(C(C)(C)C)(C)C.CO.[OH-].[Na+]>C(O)C>[CH2:15]([N:14]1[C:10]([CH2:9][OH:8])=[N:11][CH:12]=[N:13]1)[CH2:16][CH3:17]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 21187493HCID 21187493, compound

Product 1

HCID 18406849HCID 18406849, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5-(tert-butyldimethylsilanyloxymethyl)-1-propyl-1H-1,2,4-triazole (from Step a) (4.10 g, 16.1 mmol) in ethanol (18 ml) and methanol (36 ml) was added 4 M aqueous NaOH (6 ml, 24 mmol) and the mixture was stirred at room temperature for 19 h, then at 45° C. for another 5 h. The solvents were removed in vacuo and the residue was purified by flash chromatography (silica gel, EtOAc, then 10% MeOH/CH2Cl2) to leave 1.976 g (87%) of the title compound as a pale yellow oil: 1H NMR (250 MHz, CDCl3) δ 0.95 (3H, t, J=7.4 Hz), 1.91 (2H, sextet, J=7.4 Hz), 4.16 (2H, t, J=7.3 Hz), 4.76 (2H, s), 7.81 (1H, s).

Workup

  1. waitat 45° C. for another 5 h
  2. customThe solvents were removed in vacuo
  3. customthe residue was purified by flash chromatography (silica gel, EtOAc

Sources & evidence

ORD record
ord-53c5273d1f7744cc8cfa2308eeb63aa9
Source dataset
uspto-grants-2001_07
Patent number
US06255305B1

Reaction notes

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