Hydrochloric Acid → HCID 86670681, compound

HRID 1752011Notes

Reaction equation

HRID 1752011 reaction equation
I[CH2:2]CI.ICI.[Cl:8][C:9]1[CH:25]=[CH:24][C:12]([CH2:13][CH:14]2[C:18](=[O:19])[CH:17]([C:20]([F:23])([F:22])[F:21])[CH2:16][CH2:15]2)=[CH:11][CH:10]=1.[OH-].[Na+].Cl>C1COCC1>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:13][CH:14]2[C:18]3([O:19][CH2:2]3)[CH:17]([C:20]([F:21])([F:22])[F:23])[CH2:16][CH2:15]2)=[CH:24][CH:25]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6346DiiodomethaneHCID 122241,2-DiiodoethaneHCID 14798Sodium HydroxideHCID 67256161HCID 67256161, compound2×

Product 1

HCID 86670681HCID 86670681, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent4×

Procedure

Under nitrogen flow, anhydrous THF (1 ml) was combined with Sm (705 mg, 4.7 mmol), and a solution of 1,2-diiodoethane (662 mg, 2.3 mmol) dissolved in anhydrous THF (2 ml) was added dropwise with stirring. The reaction solution was stirred for 30 minutes at room temperature. Thereafter, while cooling with ice, a solution of diiodomethane (723 mg, 2.7 mmol) and 5-(4-chlorobenzyl)-2-trifluoromethylcyclopentanone (Compound (V), (Ra)Xana=H, (Rb)Xbnb=CF3, Ym=4-Cl) (432 mg, 1.6 mmol) dissolved in anhydrous THF (2 ml) was added dropwise, and stirring was continued for 2 hours at room temperature. The reaction solution was poured into a solution mixture of an aqueous solution of NaOH (NaOH (1.1 g) dissolved in 10 ml of water) and THF (10 ml), and stirring was continued for 30 minutes at room temperature. This reaction solution was combined with ice, neutralized with a 1N aqueous solution of hydrochloric acid, and then extracted with hexane. The organic layer was washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled away under reduced pressure. Silica gel chromatography (eluent; hexane:ethyl acetate=70:1) was conducted for purification to obtain the desired substance.

Workup

  1. additionwas added dropwise
  2. stirringThe reaction solution was stirred for 30 minutes at room temperature
  3. temperatureThereafter, while cooling with ice
  4. additionwas added dropwise
  5. stirringstirring
  6. stirringstirring
  7. waitwas continued for 30 minutes at room temperature
  8. extractionextracted with hexane
  9. washThe organic layer was washed with water and saturated brine
  10. dry with materialdried over anhydrous sodium sulfate
  11. distillationThe solvent was distilled away under reduced pressure
  12. customSilica gel chromatography (eluent; hexane:ethyl acetate=70:1) was conducted for purification
  13. customto obtain the desired substance

Sources & evidence

ORD record
ord-8861163e1e064ab8baf16205612b9cdf
Source dataset
uspto-grants-2015_10
Patent number
US09162966B2

Reaction notes

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