1-(Triphenylphosphoranylidene)acetone → HCID 53798873, compound

HRID 2050408Notes

Reaction equation

HRID 2050408 reaction equation
[CH3:1][S:2][C:3]1[CH:17]=[CH:16][C:6]([O:7][C:8]2[N:13]=[C:12]([CH:14]=O)[CH:11]=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.C1(P(=[CH:37][C:38](=[O:40])[CH3:39])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1C=CC=CC=1>[CH3:1][S:2][C:3]1[CH:17]=[CH:16][C:6]([O:7][C:8]2[N:13]=[C:12]([CH:14]=[CH:37][C:38](=[O:40])[CH3:39])[CH:11]=[CH:10][CH:9]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 150381-(Triphenylphosphoranylidene)acetoneHCID 12762854HCID 12762854, compound

Product 1

HCID 53798873HCID 53798873, compoundYield 221.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 29.9 g (0.122 mol) of 6-(4-(methylthio)phenoxy)picolinaldehyde and 42.7 g (0.134 mol) of triphenylphosphoranylidene-2-propanone in 750 mL of benzene was heated at reflux for 2.75 hours and cooled. The solvent was removed in vacuo leaving 77 g of an oily solid which was dissolved in methylene chloride and placed on a column of dry silica gel. The column was eluted with methylene chloride and the fractions containing the desired product were combined. The solvent was removed in vacuo leaving 32.5 g (93.7 percent of theoretical) of an oily product which slowly crystallized upon standing. The above named product melted at 71°-72.5° C.; Rf -0.53, (silica gel, 50:50 ethyl acetate-hexane), 1H NMR (CDCl3) 82.25 (s, 3H, CH3C(O)--), 2.4 (s, 3H, CH3S--) 6.7-7.75 (m, 9H, ArH and --CH=CH--).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2.75 hours
  3. temperaturecooled
  4. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-5ea6758706d543c8aeb7bb7c3dae07c6
Source dataset
uspto-grants-1991_05
Patent number
US05013352

Reaction notes

Loading…