Tetrapropylammonium → 6,6-Dimethylbicyclo[3.1.0]hexan-2-one

HRID 1432800Notes

Reaction equation

HRID 1432800 reaction equation
C([N+](CCC)(CCC)CCC)CC.[CH3:14][C:15]1([CH3:22])[CH:20]2[CH:16]1[CH2:17][CH2:18][CH:19]2[OH:21]>C(Cl)Cl>[CH3:14][C:15]1([CH3:22])[CH:20]2[CH:16]1[CH2:17][CH2:18][C:19]2=[O:21]

Participants

4

Reactant 2

HCID 9559TetrapropylammoniumHCID 12740324(+/-)-6,6-Dimethyl-bicyclo[3.1.0]hexan-2-ol

Product 1

HCID 127403286,6-Dimethylbicyclo[3.1.0]hexan-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A chilled (0° C.) solution of N-methylmorpholime N-oxide (3.11 g, 26.5 mmol) and tetrapropylammonium perrethenate (VII) (0.280 g, 0.796 mmol) in DCM (40 mL) was prepared containing 4 Å molecular sieves (ca 0.3 g). A solution of (±)-6,6-dimethyl-bicyclo[3.1.0]hexan-2-ol (1.67 g, 13.3 mmol) in DCM (10 mL) was added dropwise and the solution allowed to warm to room temperature and stirred for 1 hour under argon. The solution was filtered through a silica plug, solvent removed under reduced pressure and the resulting oil purified by column chromatography (0-100% DCM/n-hexane, silica). 6,6-Dimethyl-bicyclo[3.1.0]hexan-2-one was obtained as a brown oil. 1H NMR (CDCl3): δ 2.35-2.15 (m, 2H), 2.10-2.00 (m, 1H), 1.97-1.85 (m, 2H), 1.66 (d, 1H, J=4.7), 1.16 (s, 3H), 1.12 (s, 3H).

Workup

  1. customwas prepared
  2. additioncontaining 4 Å molecular sieves (ca 0.3 g)
  3. filtrationThe solution was filtered through a silica plug, solvent
  4. customremoved under reduced pressure
  5. customthe resulting oil purified by column chromatography (0-100% DCM/n-hexane, silica)

Sources & evidence

ORD record
ord-11b60b288a7a4b67a954d359e1058b3b
Source dataset
uspto-grants-2009_11
Patent number
US07612106B2

Reaction notes

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