1-Phenyl-1-propanone → HCID 68415318, compound

HRID 220235Notes

Reaction equation

HRID 220235 reaction equation
O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[C:15]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)(=[O:18])[CH2:16]C.[C:25]1(=O)[CH2:30][CH2:29][CH2:28][CH:27]=[CH:26]1.F[C:33](F)(F)S(O)(=O)=O>C(Cl)Cl.CCN(CC)CC>[CH3:33][C:23]1[CH:22]2[CH2:21][CH2:20][CH:19]([C:24]=1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:15](=[O:18])[CH2:16]2

Participants

7

Reactant 4

HCID 71481-Phenyl-1-propanoneHCID 135942-Cyclohexen-1-oneHCID 14812Phosphorus oxide (P4O10)HCID 62406Trifluoromethanesulfonic acid

Product 1

HCID 68415318HCID 68415318, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a suspension of 0.5 g of phosphorous pentoxide in 30 mL anh. DCM were added 1.3 mL of propiophenone followed by 2.9 mL of 2-cyclohexen-1-one at rt. The suspension was cooled to 0° C. with an ice bath before 2.6 mL of trifluoromethanesulfonic acid was carefully added. The reaction mixture was warmed to rt and then heated at 40° C. overnight. 5.4 mL of NEt3 were dropwise added at 0° C., the mixture was stirred at rt for 10 min and then evaporated to dryness. Purification by CC with EtOAc-Hept (2:8) yielded 1.2 g of rac-(1R*,4R*)-5-methyl-6-phenyl-bicyclo[2.2.2]oct-5-en-2-one as yellow oil.

Workup

  1. additionwas carefully added
  2. temperatureheated at 40° C. overnight
  3. customevaporated to dryness
  4. customPurification by CC with EtOAc-Hept (2:8)

Sources & evidence

ORD record
ord-2e35e69e95d7461e83f7a250fbd89fdc
Source dataset
uspto-grants-2012_06
Patent number
US08202885B2

Reaction notes

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