1-(Triphenylphosphoranylidene)acetone → HCID 67086773, compound

HRID 1807411Notes

Reaction equation

HRID 1807411 reaction equation
[Cl:1][C:2]1[S:3][C:4]([Cl:10])=[C:5]([Cl:9])[C:6]=1[CH:7]=O.[C:11]([CH:14]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)(=[O:13])[CH3:12]>C(#N)C.O.[Br-].[Li+]>[Cl:1][C:2]1[S:3][C:4]([Cl:10])=[C:5]([Cl:9])[C:6]=1/[CH:7]=[CH:12]/[C:11](=[O:13])[CH3:14]

Participants

6

Reactant 2

HCID 150381-(Triphenylphosphoranylidene)acetoneHCID 1737863-Thiophenecarboxaldehyde, 2,4,5-trichloro-

Product 1

HCID 67086773HCID 67086773, compoundYield 91.3%

Reagents, catalysts & solvents 3

HCID 82050Lithium BromideCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 2,4,5-trichloro-thiophene-3-carbaldehyde (10.3 g; 48 mmol) and lithium bromide (0.10 g; 1.2 mmol) in acetonitrile (100 mL) at 15° C. under nitrogen was added acetylmethylene-triphenylphosphorane (15.6 g; 49 mmol). The reaction mixture was stirred for 3 hours at ambient temperature then poured in water (200 ml) and extracted with dichloromethane (3×70 ml). Combined organic layers were dried over anhydrous sodium sulphate. The solvent was removed in vacuo and the residue was purified by chromatography over silica gel (eluant: cyclohexane/ethyl acetate 90:10) to afford 11.2 g (91% of theory) of (E)-4-(2,4,5-trichloro-thiophen-3-yl)-but-3-en-2-one as yellow solid.

Workup

  1. extractionextracted with dichloromethane (3×70 ml)
  2. dry with materialCombined organic layers were dried over anhydrous sodium sulphate
  3. customThe solvent was removed in vacuo
  4. customthe residue was purified by chromatography over silica gel (eluant: cyclohexane/ethyl acetate 90:10)

Sources & evidence

ORD record
ord-411bd0ef44fe492bb8df82547a1ba29f
Source dataset
uspto-grants-2013_01
Patent number
US08357635B2

Reaction notes

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