Diphenyl Ether → HCID 136061494, compound

HRID 861426Notes

Reaction equation

HRID 861426 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:15][N:14]=[C:13]([CH3:16])[N:12]=2)=[CH:7][CH:6]=1)C=C.[C:17]1(OC2C=CC=CC=2)[CH:22]=CC=C[CH:18]=1>C(OCC)C>[CH2:22]([C:10]1[CH:9]=[C:8]([C:11]2[O:15][N:14]=[C:13]([CH3:16])[N:12]=2)[CH:7]=[CH:6][C:5]=1[OH:4])[CH:17]=[CH2:18]

Participants

4

Reactant 2

HCID 7583Diphenyl EtherHCID 19703130HCID 19703130, compound

Product 1

HCID 136061494HCID 136061494, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

5-(4-allyloxyphenyl)-3-methyl-1,2,4-oxadiazole (1.2 g) and diphenyl ether (5 ml) were warmed gently to give a solution. This stirred solution, under an atmosphere of argon, was immersed in an oil bath at 265° C. for 12 minutes. This procedure was repeated three times. The deep red solutions were combined, diluted with diethyl ether (100 ml) and extracted with aqueous 1M sodium hydroxide (3×20 ml). The alkaline extracts were combined, washed with ether (3×30 ml), cooled in ice-water, acidified with aqueous 5M hydrochloric acid (15 ml), and extracted with ether (3×60 ml). The ether extracts were combined, washed with saturated brine (25 ml), dried (Na2SO4) and evaporated. The residue was purified by flash column chromatography on silica gel using 20% ethyl acetate/n-pentane as eluent, to give 2-allyl-4-(3-methyl-1,2,4-oxadiazol-5-yl)phenol as a solid m.p. 135°-137° C.; microanalysis, found: C, 66.7; H, 5.8; N, 12.5%; C12H12N2O2 requires: C, 66.7; H, 5.6; N, 13.0%; NMR: 2.3-2.35(3H,s), 3.3-3.4(2H,d), 5.0-5.15(2H,m), 5.85-6.1(1H,m), 6.95-7.05(1H,d), 7.75-7.8(2H,m) and 10.4-10.5(1H,s); m/z 217 (M+H).

Workup

  1. customto give a solution
  2. extractionextracted with aqueous 1M sodium hydroxide (3×20 ml)
  3. washwashed with ether (3×30 ml)
  4. temperaturecooled in ice-water
  5. extractionextracted with ether (3×60 ml)
  6. washwashed with saturated brine (25 ml)
  7. dry with materialdried (Na2SO4)
  8. customevaporated
  9. customThe residue was purified by flash column chromatography on silica gel using 20% ethyl acetate/n-pentane as eluent

Sources & evidence

ORD record
ord-3688d9c85d8141a38d38e34e8ad81a1a
Source dataset
uspto-grants-1998_02
Patent number
US05714496

Reaction notes

Loading…