Acetyl chloride → HCID 21265653, compound

HRID 566178Notes

Reaction equation

HRID 566178 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[C:5]1([C:11]2[C:12](=[O:19])[CH:13]3[CH:17]([CH:18]=2)[CH2:16][CH2:15][CH2:14]3)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>ClCCl>[C:1]([C:8]1[CH:7]=[CH:6][C:5]([C:11]2[C:12](=[O:19])[CH:13]3[CH:17]([CH:18]=2)[CH2:16][CH2:15][CH2:14]3)=[CH:10][CH:9]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 11252606HCID 11252606, compound

Product 1

HCID 21265653HCID 21265653, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of Perrier complex was prepared from acetyl chloride (663mg, 8.45 mmol) and aluminimum chloride (1.13 g, 8.45 mmol) in dichloromethane (5 ml) and 4,5,6,6a-tetrahydro-2-phenyl-1(3aH)pentalenone (335 mg, 1.69mmol) in dichloromethane (95 ml) was added at 0° C. The mixture was heated under reflux for 48 h, then poured onto ice, extracted with dichloromethane and the extract washed with aqueous potassium carbonate and dried (MgSO4). After removal of solvent the residue was chromatographed. Ethyl acetate—n-hexane (1:2) eluted unreacted starting ketone (17 mg) followed by the title product (277 mg, 68%), yellowish crystals, m.p. 76-77° C.

Workup

  1. additionwas added at 0° C
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 48 h
  4. additionpoured onto ice
  5. extractionextracted with dichloromethane
  6. washthe extract washed with aqueous potassium carbonate
  7. dry with materialdried (MgSO4)
  8. customAfter removal of solvent the residue
  9. customwas chromatographed
  10. washEthyl acetate—n-hexane (1:2) eluted unreacted

Sources & evidence

ORD record
ord-33ec8ca5ad534ce982e4c6477ca8e4a2
Source dataset
uspto-grants-2001_01
Patent number
US06174840B1

Reaction notes

Loading…