Benzyl Alcohol → Benzyl 3-methyl-1,2,4-oxadiazol-5-yl-acetate

HRID 971707Notes

Reaction equation

HRID 971707 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.[CH2:16](O)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CCCCCC>C1(C)C=CC=CC=1.C(OCC)C.C1(C)C=CC=CC=1.C1(C)C=CC=CC=1.CCCCCC>[CH3:6][C:7]1[N:11]=[C:10]([CH2:12][C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[O:9][N:8]=1

Participants

8

Reactant 4

HCID 244Benzyl AlcoholHCID 8058HexaneHCID 24813Phosphorus oxychlorideHCID 213130182-(3-Methyl-1,2,4-oxadiazol-5-yl)acetic acid

Product 1

HCID 54522900Benzyl 3-methyl-1,2,4-oxadiazol-5-yl-acetateYield 47%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 21889329Toluene hexaneSolvent2×HCID 22238780Ether tolueneSolvent

Conditions

Temperature
40 °C

Procedure

Using the procedure of Example 17, 8 g of phosphorous oxychloride were slowly added to a mixture of 8 g of 3-methyl-1,2,4-oxadiazol-5-yl-acetic acid and 6.2 g of dry benzyl alcohol with the rate of addition adjusted to a reaction temperature of 40°-45° C. The resulting reaction mixture was stirred for 5 hours at 40° C. and then was treated in the usual manner. The obtained yellow oil was submitted to column chromatography over silica employing as eluents n-hexane and 3:1 hexane-toluene-, 1:1-toluene-hexane, 3:1 toluene-hexane mixture, toluene and finally a 3:1 toluene-diethyl ether mixture. The finally obtained colorless oil was 6.1 g (47% yield) of benzyl 3-methyl-1,2,4-oxadiazol-5-yl-acetate with a purity of about 95% (according to TLC and PMR spectrum) and a refractive index nD25 =1.518.

Workup

  1. customadjusted to a reaction temperature of 40°-45° C
  2. customThe resulting reaction mixture
  3. additionwas treated in the usual manner

Sources & evidence

ORD record
ord-965dc40002074e4e92e17a6e05a8929b
Source dataset
uspto-grants-1979_07
Patent number
US04160829

Reaction notes

Loading…