(+-)-2-Butanol → Sec.-butyl 3-methyl-1,2,4-oxadiazol-5-yl-acetate

HRID 971706Notes

Reaction equation

HRID 971706 reaction equation
P(Cl)(Cl)(Cl)=O.[CH3:6][C:7]1[N:11]=[C:10]([CH2:12][C:13]([OH:15])=[O:14])[O:9][N:8]=1.[CH:16](O)([CH2:18][CH3:19])[CH3:17]>>[CH3:6][C:7]1[N:11]=[C:10]([CH2:12][C:13]([O:15][CH:16]([CH2:18][CH3:19])[CH3:17])=[O:14])[O:9][N:8]=1

Participants

4

Reactant 3

HCID 6568(+-)-2-ButanolHCID 24813Phosphorus oxychlorideHCID 213130182-(3-Methyl-1,2,4-oxadiazol-5-yl)acetic acid

Product 1

HCID 131711576Sec.-butyl 3-methyl-1,2,4-oxadiazol-5-yl-acetateYield 36.4%

Conditions

Temperature
65 °C

Procedure

Using the procedure of Example 17, 12 g of phosphorous oxychloride were slowly added to a mixture of 12 g of 3-methyl-1,2,4-oxadiazol-5-yl-acetic acid and 8.9 g of dry sec.-butanol and the rate of addition was adjusted to a reaction temperature of 65°±5° C. The resulting reaction mixture was stirred for 90 minutes at 65° C., and then treated as in Example 17. The product was distilled at 68° C. and 1.5 mm Hg to obtain 6.1 g (35% yield) of sec.-butyl 3-methyl-1,2,4-oxadiazol-5-yl-acetate. The purity of the final product was about 95% (according to TLC and PMR spectrum) and it had a refractive index nD25 =1.438.

Workup

  1. additionthe rate of addition
  2. customwas adjusted to a reaction temperature of 65°±5° C
  3. customThe resulting reaction mixture
  4. additiontreated as in Example 17
  5. distillationThe product was distilled at 68° C.

Sources & evidence

ORD record
ord-14742229ec634d9a8256cc1036fba92e
Source dataset
uspto-grants-1979_07
Patent number
US04160829

Reaction notes

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