Ethyl orthoformate → 2-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,4-oxadiazole

HRID 1531391Notes

Reaction equation

HRID 1531391 reaction equation
[CH3:1][C:2]1([CH3:19])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:18]=[CH:17][C:12]([C:13]([NH:15][NH2:16])=[O:14])=[CH:11][CH:10]=2)[O:3]1.[CH:20](OCC)(OCC)OCC>C(O)C>[CH3:8][C:6]1([CH3:7])[C:2]([CH3:19])([CH3:1])[O:3][B:4]([C:9]2[CH:18]=[CH:17][C:12]([C:13]3[O:14][CH:20]=[N:16][N:15]=3)=[CH:11][CH:10]=2)[O:5]1

Participants

4

Reactant 2

HCID 31214Ethyl orthoformateHCID 212539794-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzohydrazide

Product 1

HCID 212539742-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,4-oxadiazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

10 g (38 mmol) of 2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-benzohydrazide are dissolved in 30 g (20 mmol) of triethyl orthoformate, and the mixture is heated to reflux. The ethanol formed during the reaction is continuously removed by distillation. After the mixture has cooled, the product crystallizes out, is filtered off and washed with a little ethanol. Yield: 8.7 g (32 mmol, 84%). An analogous procedure is carried out using the compounds of the formula (II) shown in Table 4.

Workup

  1. temperaturethe mixture is heated to reflux
  2. customis continuously removed by distillation
  3. temperatureAfter the mixture has cooled
  4. customthe product crystallizes out
  5. filtrationis filtered off
  6. washwashed with a little ethanol

Sources & evidence

ORD record
ord-3c79c8c679bc4b2d813165866d68f6b8
Source dataset
uspto-grants-2001_03
Patent number
US06197967B1

Reaction notes

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