Water → HCID 11240937, compound

HRID 985732Notes

Reaction equation

HRID 985732 reaction equation
C(OCC)C.O[CH:7]([CH2:16][C:17]([CH2:20][Si](C)(C)C)=[C:18]=[CH2:19])[CH2:8][CH2:9][CH:10]1[CH2:14][CH2:13][CH2:12][C:11]1=[O:15].[Si](OS(C(F)(F)F)(=O)=O)(C)(C)C.O>CCOC(C)=O>[CH2:20]=[C:17]1[C:18](=[CH2:19])[C:11]23[O:15][CH:7]([CH2:8][CH2:9][CH:10]2[CH2:14][CH2:13][CH2:12]3)[CH2:16]1

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 65367Trimethylsilyl triflateHCID 121566822-(3-hydroxy-5-trimethylsilanylmethyl-hepta-5,6-dienyl)-cyclopentanone

Product 1

HCID 11240937HCID 11240937, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

1.50 mL of diethyl ether was added to 2-(3-hydroxy-5-trimethylsilanylmethyl-hepta-5,6-dienyl)-cyclopentanone (98 mg, 0.35 mmol) under nitrogen atmosphere. While stirring at −78° C., TMSOTf (63 μL, 0.35 mmol) was added. While stirring the reaction mixture, the reaction temperature was slowly increased to room temperature for 3 hours. The reaction mixture was stirred at room temperature for 30 minutes. After the reaction was completed, H2O was added. After stirring for about 5 minutes, the reaction mixture was diluted with EtOAc and washed with water and saturated brine. The organic layer was separated from the reaction mixture and dried with anhydrous MgSO4. The solvent was removed under reduced pressure and the remaining material was purified with column chromatography (EtOAc/n-hexane={fraction (1/15)}) to obtain 60 mg of the pro duct (91%).

Workup

  1. stirringWhile stirring the reaction mixture
  2. temperaturethe reaction temperature was slowly increased to room temperature for 3 hours
  3. stirringThe reaction mixture was stirred at room temperature for 30 minutes
  4. stirringAfter stirring for about 5 minutes
  5. washwashed with water and saturated brine
  6. customThe organic layer was separated from the reaction mixture
  7. dry with materialdried with anhydrous MgSO4
  8. customThe solvent was removed under reduced pressure
  9. customthe remaining material was purified with column chromatography (EtOAc/n-hexane={fraction (1/15)})
  10. customto obtain 60 mg of the pro duct (91%)

Sources & evidence

ORD record
ord-4f0f9e5278cb4f30901e805103c746c9
Source dataset
uspto-grants-2005_03
Patent number
US06872840B1

Reaction notes

Loading…