1-(Triphenylphosphoranylidene)acetone → HCID 13726877, compound

HRID 1583886Notes

Reaction equation

HRID 1583886 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[S:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH:7]=O)([O-:3])=[O:2].C1(P(C2C=CC=CC=2)(C2C=CC=CC=2)=[CH:24][C:25](=[O:27])[CH3:26])C=CC=CC=1>O>[N+:1]([C:4]1[CH:5]=[C:6](/[CH:7]=[CH:24]\[C:25](=[O:27])[CH3:26])[CH:9]=[CH:10][C:11]=1[S:12][CH2:13][CH2:14][CH2:15][CH3:16])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 150381-(Triphenylphosphoranylidene)acetoneHCID 13726875HCID 13726875, compound

Product 1

HCID 13726877HCID 13726877, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(i) A mixture of 3-nitro-4-(n-butylthio)-benzaldehyde (12.0 g), 1-triphenylphosphoranylidene-2-propanone (1.2 equiv.) dimethyl sulfoxide (300 ml) was stirred at ambient temperature for 24 hr. The solution was poured into water (1 liter) and the resulting mixture was extracted with ethyl acetate. The dried (MgSO4) organic extract was evaporated under reduced pressure and the residue was purified by column chromatography over silica with chloroform elution to give cis-1-[3-nitro-4-(n-butylthio)phenyl]but-1-en-3-one, mp 100° C. Pmr spectrum (CDCl3 ; δ in ppm): 0.97 (3H, t); 1.63 (4H, m); 2.40 (3H, s); 2.98 (2H, t); 6.75 (1H, d); 7.38-7.75 (3H, m); 8.36 (1H, d).

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. dry with materialThe dried (MgSO4)
  3. extractionorganic extract
  4. customwas evaporated under reduced pressure
  5. customthe residue was purified by column chromatography over silica with chloroform elution

Sources & evidence

ORD record
ord-f7d0eff7658b4e74981b97e40edfe1e8
Source dataset
uspto-grants-1985_11
Patent number
US04555263

Reaction notes

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