Ethylorthoformate → HCID 21448189, compound

HRID 596774Notes

Reaction equation

HRID 596774 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=[CH:7][C:8](=[N:10][OH:11])[NH2:9].[CH:12]([O-])([O-])OCC>B(F)(F)F.CCOCC>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1/[CH:6]=[CH:7]/[C:8]1[N:9]=[CH:12][O:11][N:10]=1

Participants

4

Reactant 2

HCID 53630039EthylorthoformateHCID 53720242HCID 53720242, compound

Product 1

HCID 21448189HCID 21448189, compound

Reagents, catalysts & solvents 1

HCID 8000Boron trifluoride etherateCatalyst

Procedure

β-(Thien-2-yl) acrylamidoxime (2.20 g.) was refluxed in ethyl orthoformate (30 ml.) containing one drop of boron trifluoride etherate. After 1 hr. the ethyl orthoformate was removed under reduced pressure and the residue was dissolved in chloroform (20 ml.) and washed consecutively with 2N hydrochloric acid (20 ml.), saturated sodium hydrogen carbonate solution (20 ml.), and water (20 ml.). Evaporation of the chloroform solution to dryness and chromatography in benzene on silica gel gave trans-1-(thien-2-yl)-2-(1,2,4-oxadiazol-3-yl)-ethylene 1.57 g. (67%), m.p. 78° , λmax. (EtOH) 306 nm, (ε 21700) (Found: C, 52.9; H, 3.7; N, 15.3; S, 17.2. C8H6N2OS requires C, 53.9; H, 3.4; N, 15.7; S, 18.0%).

Workup

  1. customthe ethyl orthoformate was removed under reduced pressure
  2. dissolutionthe residue was dissolved in chloroform (20 ml.)
  3. washwashed consecutively with 2N hydrochloric acid (20 ml.), saturated sodium hydrogen carbonate solution (20 ml.), and water (20 ml.)
  4. customEvaporation of the chloroform solution to dryness and chromatography in benzene on silica gel

Sources & evidence

ORD record
ord-48fdd9bd231a4958ac3bf6bf6ce9a30a
Source dataset
uspto-grants-1977_03
Patent number
US04012377

Reaction notes

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