HCID 18755519, compound → HCID 18755516, compound

HRID 1838642Notes

Reaction equation

HRID 1838642 reaction equation
[CH3:1][C:2]1(SC)[CH:8]2[CH:6]([CH2:7]2)[C:5](=[O:9])[CH2:4][C:3]1=[O:10]>CO.[Ni]>[CH3:1][C:2]1[C:3](=[O:10])[CH2:4][C:5](=[O:9])[CH2:6][CH2:7][CH:8]=1

Participants

4

Reactant 1

HCID 18755519HCID 18755519, compound

Product 1

HCID 18755516HCID 18755516, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

1.0 g (5.4 mmol) of the 5-methyl-5-methylsulfanylbicyclo[4.1.0]heptane-2,4-dione isomers II is hydrogenated for 90 minutes under atmospheric pressure in 15 ml of methanol in the presence of 5 g Raney nickel. The mixture is concentrated and purified over silica gel (mobile phase ethyl acetate/hexane 1:1), and 4-methylcyclohept-4-ene-1,3-dione, 1H-NMR (CDCl3): 6.84, m, CH, 3.94, s, CH2, 2.77, m, CH2, 2,59, m, CH2, 1.88 ppm, s, CH3, is obtained as an oil.

Workup

  1. concentrationThe mixture is concentrated
  2. custompurified over silica gel (mobile phase ethyl acetate/hexane 1:1), and 4-methylcyclohept-4-ene-1,3-dione, 1H-NMR (CDCl3): 6.84, m, CH, 3.94
  3. customCH3, is obtained as an oil

Sources & evidence

ORD record
ord-283de42d1b97418089ad0e3532fd6c39
Source dataset
uspto-grants-2004_01
Patent number
US06673938B1

Reaction notes

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