Pivaloyl chloride → HCID 23358677, compound

HRID 232513Notes

Reaction equation

HRID 232513 reaction equation
N1[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[N:4][N:3]=N1.[C:11](Cl)(=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13]>C1(C)C=CC=CC=1>[C:12]([C:11]1[O:16][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[N:4][N:3]=1)([CH3:15])([CH3:14])[CH3:13]

Participants

4

Reactant 2

HCID 62493Pivaloyl chlorideHCID 178470518HCID 178470518, compound

Product 1

HCID 23358677HCID 23358677, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of ethyl tetrazole-5-carboxylate (8.53 g, 60 mmol) and pivaloyl chloride (7.23 g, 60 mmol) in dry toluene (240 ml) is refluxed for 16 hours. After the solution has cooled to room temperature, it is washed two times with 1 N sodium hydroxide solution (20 ml) and then once with water (20 ml). The organic phase is dried over magnesium sulphate and the solvent is evaporated in vacuo to give ethyl 5-tert-butyl-[1,3,4]oxadiazole-2-carboxylate as a red oil (6.96 g, 59%), which is used in the following stage without further purification.

Workup

  1. washit is washed two times with 1 N sodium hydroxide solution (20 ml)
  2. dry with materialThe organic phase is dried over magnesium sulphate
  3. customthe solvent is evaporated in vacuo

Sources & evidence

ORD record
ord-e23c033927d345e494a2d38ec380f669
Source dataset
uspto-grants-1997_01
Patent number
US05591695

Reaction notes

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