Dimethyl Sulfide → 5,5-Dimethyl-2-phenylcyclopent-2-en-1-one

HRID 325188Notes

Reaction equation

HRID 325188 reaction equation
[CH3:1][C:2]([CH3:15])([CH2:12][CH:13]=C)[C:3](=[O:11])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.O=[O+][O-].O=O.CSC.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1CCN2C(=NCCC2)CC1>CO.C(Cl)Cl.CC(O)=O>[CH3:15][C:2]1([CH3:1])[C:3](=[O:11])[C:4]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=2)=[CH:13][CH2:12]1

Participants

9

Reactant 5

HCID 1068Dimethyl SulfideHCID 11776TriphenylphosphineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 153393703,3-Dimethyl-1-phenylhex-5-en-2-oneHCID 131711318Oxygen ozone

Product 1

HCID 125706695,5-Dimethyl-2-phenylcyclopent-2-en-1-oneYield 79.6%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of the product of Step 2 (15 g) in 70 mL of MeOH and 50 mL of CH2Cl2 was treated with a stream of ozone/oxygen until the solution turned light blue. Dimethylsulfide (20 mL) was added and the reaction mixture was stirred for 2 h at room temperature and then treated with 5 g of triphenylphosphine for an additional 0.5 h. DBU (1 mL) was then added to the reaction mixture. After stirring for 1 h at room temperature, 1 mL of AcOH was added and the reaction mixture was concentrated. The residue was dissolved in 100 mL of 20:1 hexanes/EtOAc and the solution was filtered through a pad of silica gel. The filtrate was concentrated to give 11 g of the tite compound as a yellow oil.

Workup

  1. stirringAfter stirring for 1 h at room temperature
  2. concentrationthe reaction mixture was concentrated
  3. dissolutionThe residue was dissolved in 100 mL of 20:1 hexanes/EtOAc
  4. filtrationthe solution was filtered through a pad of silica gel
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-3ba58c157a474edda1f28edb5a1b4be2
Source dataset
uspto-grants-2001_04
Patent number
US06222048B1

Reaction notes

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