Sodium Sulfite → HCID 57771496, compound

HRID 2070559Notes

Reaction equation

HRID 2070559 reaction equation
[CH3:1][C:2]1([CH3:14])[C:7]2([CH2:12][CH:11]([OH:13])[CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH2:4][CH2:3]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O.S([O-])([O-])=O.[Na+].[Na+]>C(Cl)(Cl)Cl>[CH3:1][C:2]1([CH3:14])[C:7]2([CH2:12][C:11](=[O:13])[CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 24437Sodium SulfiteHCID 159087TriacetoxyperiodinaneHCID 57771393HCID 57771393, compound

Product 1

HCID 57771496HCID 57771496, compoundYield 91.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of 11,11-dimethyl-spiro[5.5]undec-7-en-2-ol (320 mg) obtained in Step 4 in chloroform (10 mL) was added 1,1,1-tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-on e (Dess-Martin periodinane; 735 mg) under ice-cooling, followed by stirring the reaction mixture under ice-cooling for 3 hours. Then, after addition of aqueous sodium sulfite solution to the reaction mixture, chloroform was evaporated off in vacuo. To the residue was added aqueous sodium bicarbonate solution, followed by extraction with ethyl acetate. The organic layer was washed with water, dried and concentrated. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate (volume ratio)=20:1) to give 11,11-dimethyl-spiro[5.5]undec-7-en-2-one (290 mg).

Workup

  1. temperaturecooling
  2. temperaturecooling for 3 hours
  3. customwas evaporated off in vacuo
  4. additionTo the residue was added aqueous sodium bicarbonate solution
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe organic layer was washed with water
  7. customdried
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate (volume ratio)=20:1)

Sources & evidence

ORD record
ord-c7f014b71b21417f81ac972614f78d7f
Source dataset
uspto-grants-2012_10
Patent number
US08299296B2

Reaction notes

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