Sodium Sulfite → HCID 57771463, compound

HRID 2070605Notes

Reaction equation

HRID 2070605 reaction equation
[Si:1]([O:8][CH2:9][CH:10]1[CH2:15][CH2:14][CH:13]([CH2:16][OH:17])[CH2:12][CH2:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O.S([O-])([O-])=O.[Na+].[Na+].C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[Si:1]([O:8][CH2:9][CH:10]1[CH2:11][CH2:12][CH:13]([CH:16]=[O:17])[CH2:14][CH2:15]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 24437Sodium SulfiteHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 10753723[4-({[tert-Butyl(dimethyl)silyl]oxy}methyl)cyclohexyl]methanol

Product 1

HCID 57771463HCID 57771463, compoundYield 81.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of [4-(tert-butyldimethylsilanyloxymethyl)-cyclohexyl]-methanol (8.5 g) obtained in Step 1 in chloroform (85 mL) was added 1,1,1-tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one (Dess-Martin periodinane; 15.3 g) under ice-cooling, followed by stirring the mixture under ice-cooling for 2.5 hours. After addition of aqueous sodium sulfite solution and aqueous sodium bicarbonate solution, the reaction mixture was filtered through Celite, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, dried and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane (volume ratio)=1:19 to 1:9) to give 4-(tert-butyldimethylsilanyloxymethyl)-cyclohexanecarbaldehyde (6.9 g).

Workup

  1. temperaturecooling
  2. temperaturecooling for 2.5 hours
  3. filtrationthe reaction mixture was filtered through Celite
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography on silica gel (ethyl acetate:hexane (volume ratio)=1:19 to 1:9)

Sources & evidence

ORD record
ord-182680e64d204e1cbf406aa40abfb27e
Source dataset
uspto-grants-2012_10
Patent number
US08299296B2

Reaction notes

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