Hydrochloric Acid → HCID 9927503, compound

HRID 2293289Notes

Reaction equation

HRID 2293289 reaction equation
[Li].[F:2][C:3]1[CH:20]=[CH:19][C:6]([C:7]([C:9]2[CH:14]=[CH:13][C:12]([S:15]([CH3:18])(=[O:17])=[O:16])=[CH:11][CH:10]=2)=O)=[CH:5][CH:4]=1.[C:21]1(=O)[CH2:25][CH2:24][CH2:23][CH2:22]1.Cl>COCCOC.[Cl-].[Cl-].[Cl-].[Ti+3]>[C:21]1(=[C:7]([C:6]2[CH:19]=[CH:20][C:3]([F:2])=[CH:4][CH:5]=2)[C:9]2[CH:14]=[CH:13][C:12]([S:15]([CH3:18])(=[O:17])=[O:16])=[CH:11][CH:10]=2)[CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8452CyclopentanoneHCID 3028194LithiumHCID 10107581HCID 10107581, compound

Product 1

HCID 9927503HCID 9927503, compoundYield 44.8%

Reagents, catalysts & solvents 2

HCID 10313229titanium(III) trichlorideCatalystHCID 80711,2-DimethoxyethaneSolvent2×

Procedure

3.5 g (500 mmol) of lithium are added to a suspension of 25.4 g (165 mmol) of titanium trichloride in 300 ml of 1,2-dimethoxyethane. The mixture is refluxed for 2 hours and then cooled to room temperature. A solution of 7.5 g (27 mmol) of 4-fluoro-4'-methylsulfonylbenzophenone, prepared in Example 2, and 2.25 g (27 mmol) of cyclopentanone in 80 ml of 1,2-dimethoxyethane is added dropwise and the mixture is refluxed for 8 hours. After cooling, the mixture is treated with dilute hydrochloric acid solution and extracted with t-butyl methyl ether. The organic phase is dried over magnesium sulfate and evaporated under vacuum to give a residue, which is chromatographed on silica gel in dichloromethane. The resulting oil crystallizes from an isopropyl ether/pentane mixture to give 4 g of 4-[(cyclopentylidene)(4-fluorophenyl)methyl]methylsulfonylbenzene in the form of crystals melting at 84°-85° C.

Workup

  1. temperatureThe mixture is refluxed for 2 hours
  2. additionis added dropwise
  3. temperaturethe mixture is refluxed for 8 hours
  4. temperatureAfter cooling
  5. extractionextracted with t-butyl methyl ether
  6. dry with materialThe organic phase is dried over magnesium sulfate
  7. customevaporated under vacuum
  8. customto give a residue, which
  9. customis chromatographed on silica gel in dichloromethane
  10. customThe resulting oil crystallizes from an isopropyl ether/pentane mixture

Sources & evidence

ORD record
ord-1f99d0e3b42d4c1787091eb72fac8d3d
Source dataset
uspto-grants-1997_11
Patent number
US05686460

Reaction notes

Loading…