Hydrochloric Acid → HCID 178447810, compound

HRID 1766956Notes

Reaction equation

HRID 1766956 reaction equation
S(Cl)(Cl)=O.[CH2:5]([C@H:8]1[CH2:13][CH2:12][C@H:11]([CH:14]([CH2:18][C:19]2[CH:24]=[C:23]([F:25])[C:22]([F:26])=[C:21]([F:27])[CH:20]=2)[C:15](O)=[O:16])[CH2:10][CH2:9]1)[CH2:6][CH3:7].[Cl-].[Al+3].[Cl-].[Cl-].Cl>ClCCl>[F:25][C:23]1[CH:24]=[C:19]2[C:20](=[C:21]([F:27])[C:22]=1[F:26])[C:15](=[O:16])[CH:14]([C@H:11]1[CH2:10][CH2:9][C@H:8]([CH2:5][CH2:6][CH3:7])[CH2:13][CH2:12]1)[CH2:18]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 6451240Aluminum(III) ChlorideHCID 178447954HCID 178447954, compound

Product 1

HCID 178447810HCID 178447810, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Dichloromethane (25 ml) and thionyl chloride (20 ml) were added to 2-(trans-4-propylcyclohexyl)-3-(3,4,5-trifluorophenyl)propionic acid crude product (12.3 g), and refluxed while heating for 4 hours. The dichloromethane was distilled off at normal pressure and the thionyl chloride was distilled off under reduced pressure followed by the addition of dichloromethane (50 ml) to the residue to prepare a dichloromethane solution of 2-(trans-4-propylcyclohexyl)-3-(3,4,5-trifluorophenyl)propionic acid chloride. This was then dropped in to a dichloromethane suspension (20 ml) of aluminum chloride (8 g) at room temperature over the course of 30 minutes. Moreover, after stirring for 2 hours, the reaction solution was poured into 10% hydrochloric acid while cooling with ice. The organic layer was concentrated after drying with anhydrous sodium sulfate. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1) to obtain 5,6,7-trifluoro-2-(trans-4-propylcyclohexyl)-1-indanone crude product (8.8 g, purity: 73%). This was then recrystallized from ethanol to obtain 5,6,7-trifluoro-2-(trans-4-propylcyclohexyl)-1-indanone (5 g, purity: 99%). This compound had a molecular weight of 310 as determined by mass analysis.

Workup

  1. temperaturerefluxed
  2. temperaturewhile heating for 4 hours
  3. distillationThe dichloromethane was distilled off at normal pressure
  4. distillationthe thionyl chloride was distilled off under reduced pressure
  5. additionfollowed by the addition of dichloromethane (50 ml) to the residue
  6. customto prepare a dichloromethane solution of 2-(trans-4-propylcyclohexyl)-3-(3,4,5-trifluorophenyl)propionic acid chloride
  7. temperaturewhile cooling with ice
  8. concentrationThe organic layer was concentrated
  9. dry with materialafter drying with anhydrous sodium sulfate
  10. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-acaa809c8adf4986a8bf86a94ebf3280
Source dataset
uspto-grants-2007_06
Patent number
US07232592B2

Reaction notes

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