Dimethylformamide → HCID 14798984, compound

HRID 345864Notes

Reaction equation

HRID 345864 reaction equation
[NH:1]1[CH:5]=[N:4][CH:3]=[N:2]1.CC(C)([O-])C.[K+].[C:12]([C:14]1([C:17]2([CH2:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:19][O:18]2)[CH2:16][CH2:15]1)#[N:13].CN(C=O)C>C(OCC)(=O)C>[C:12]([C:14]1([C:17]([OH:18])([CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:19][N:1]2[CH:5]=[N:4][CH:3]=[N:2]2)[CH2:15][CH2:16]1)#[N:13]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 92571H-1,2,4-TriazoleHCID 14798966HCID 14798966, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 14798984HCID 14798984, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

0.8 g (12 mmol) of 1,2,4-triazole, 0.1 g (1 mmol) of potassium tert.-butoxide and 0.8 g (4 mmol) of 2-(1-cyanocyclopropyl)-2-(2-phenylethyl)oxirane (IV-16, Example 34) are heated to 80° C. for 6 h in 10 ml of abs. DMF. The solvent is stripped off in vacuo, and the residue is taken up in ethyl acetate and washed with water. After drying over Na2SO4, the solvent is evaporated in vacuo and the residue is chromatographed on silica gel (CH2Cl3 containing 2% ethanol). 0.3 g (28% of theory) of 2-(1-cyanocyclopropyl)-4-phenyl-1-(1,2,4-triazol- 1-yl)butan-2-ol is obtained in the form of a colorless oil, 1H--NMR (CDCl3):

Workup

  1. washwashed with water
  2. dry with materialAfter drying over Na2SO4
  3. customthe solvent is evaporated in vacuo
  4. customthe residue is chromatographed on silica gel (CH2Cl3 containing 2% ethanol)

Sources & evidence

ORD record
ord-f69a343d7a614455aaa0379dc03f516b
Source dataset
uspto-grants-1991_10
Patent number
US05059615

Reaction notes

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