Sodium Hydroxide → HCID 54481442, compound

HRID 1657040Notes

Reaction equation

HRID 1657040 reaction equation
[OH-].[Na+].[CH3:3][C:4]1([CH3:11])[CH2:8][CH:7]([Cl:9])[CH2:6][C:5]1=[O:10].[F:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][CH:14]=1>C(O)C>[CH3:3][C:4]1([CH3:11])[CH2:8][CH:7]([Cl:9])[C:6](=[CH:17][C:16]2[CH:19]=[CH:20][C:13]([F:12])=[CH:14][CH:15]=2)[C:5]1=[O:10]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 680234-FluorobenzaldehydeHCID 19042352HCID 19042352, compound

Product 1

HCID 54481442HCID 54481442, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

10% strength aqueous sodium hydroxide solution (50 cc) is added to a mixture of 2,2-dimethyl-4-chloro-1-cyclopentanone (10 g) and 4-fluorobenzaldehyde (8.4 g) in ethanol (100 c) at 0° C. After 30 minutes, a thick slurry is filtered and the solid washed and then dried. 2,2-Dimethyl-4-chloro-5-(4-fluorobenzylidene)-1-cyclopentanone (11.8 g), m.p. 69° C., is obtained. Sodium hydride (3.1 g; 80% strength dispersion in mineral oil) in anhydrous DMSO (50 cc) is heated to 80° C. until the solid is dissolved completely. The solution is then diluted with THF (100 cc) and thereafter cooled to -10° C. A solution of trimethylsulphonium iodide (11.5 g) in dimethyl sulphoxide (80 cc) is added to the mixture in the course of 10 minutes and the mixture is stirred for o15 minutes at -10° C. A solution of 2,2-dimethyl-4-chloro- 5-(4-fluorobenzylidene) -1-cyclopentanone (11.8 g) is then added in THF (100 cc). The mixture thereby produced is left at room temperature, then poured into water and extracted with ether, washed with water, dried and distilled. 7-(4-Fluorobenzylidene)-4,4-dimethyl-1-oxaspiro [2.4]hept-5-ene, used directly for the next step, is obtained.

Workup

  1. filtrationa thick slurry is filtered
  2. washthe solid washed
  3. customdried

Sources & evidence

ORD record
ord-ef33248cdcf74488aeb191c1a36957d4
Source dataset
uspto-grants-1993_10
Patent number
US05256683

Reaction notes

Loading…