Acetone → HCID 12972319, compound

HRID 49158Notes

Reaction equation

HRID 49158 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:6]3[CH2:14][CH:9]([CH2:10][C:11]=2[C:12]=1[F:13])C=C3.C[N+]1([O-])[CH2:21][CH2:20][O:19]CC1.CC(C)=[O:25]>O.[Os](=O)(=O)(=O)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:6]3[CH2:14][CH:9]([CH2:10][C:11]=2[C:12]=1[F:13])[CH:21]([OH:25])[CH:20]3[OH:19]

Participants

6

Reactant 3

HCID 180AcetoneHCID 82029Methyl morpholine oxideHCID 129723185,6-Difluorotricyclo[7.2.1.02,7]dodeca-2(7),3,5,10-tetraene

Product 1

HCID 12972319HCID 12972319, compound

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent

Procedure

5,6-Difluorotricyclo[7.2.1.02,7]dodeca-2(7),3,5,10-tetraene (714 mg, 3.72 mmol) and N-methyl morpholine N-oxide (553 mg, 4.10 mmol) were stirred in acetone (20 mL) and H2O (3 mL). To this was added a solution of osmium tetraoxide (OsO4) (0.2 mL, 2.5% wt. soln. in t-butanol (t-BuOH), 0.02 mmol). After 18 hours, the mixture was concentrated to an oil, dissolved In a minimum of CH2Cl2 and filtered through a silica pad (3×3 mm) eluting with 20% EtOAc/hexanes. Product containing fractions were concentrated to an oil (850 mg, 100%). (TLC 20% EtOAc/hexanes Rf 0.37). 1H NMR (CDCl3) δ 6.88 (ddd, J=9.3, 8.5, 7.6 Hz, 1H), 6.78 (m, 1H), 4.01 (AB d, 2H), 3.08 (br s, 1H), 2.92 (AB dd, J=17.9, 5.0 Hz, 1H), 2.75 (br AB, J=17.9 Hz, 1H), 2.44 (br s, 1H), 2.32 (2-OH), 2.28 (m, 1H), 1.50 (d, J=7.8 Hz, 1H). GCMS m/e 226 (M+).

Workup

  1. concentrationthe mixture was concentrated to an oil
  2. dissolutiondissolved In a minimum of CH2Cl2
  3. filtrationfiltered through a silica pad (3×3 mm)
  4. washeluting with 20% EtOAc/hexanes
  5. additionProduct containing fractions
  6. concentrationwere concentrated to an oil (850 mg, 100%)

Sources & evidence

ORD record
ord-128ec55480d8411aad367e63dcc1eceb
Source dataset
uspto-grants-2004_03
Patent number
US06706702B2

Reaction notes

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