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

HRID 1295066Notes

Reaction equation

HRID 1295066 reaction equation
C[N+]1([O-])CCOCC1.C([N+](CCC)(CCC)CCC)CC.[CH3:22][C:23]1([CH3:30])[CH:28]2[CH:24]1[CH2:25][CH2:26][CH:27]2[OH:29]>C(Cl)Cl>[CH3:22][C:23]1([CH3:30])[CH:28]2[CH:24]1[CH2:25][CH2:26][C:27]2=[O:29]

Participants

5

Reactant 3

HCID 9559TetrapropylammoniumHCID 82029Methyl morpholine oxideHCID 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-methylmorpholine 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-2a80789ba79f4ff7ba956cecdc354633
Source dataset
uspto-grants-2007_07
Patent number
US07241792B2

Reaction notes

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