Sodium Thiosulfate → 4-(2,5,5-Trimethyl-[1,3]dioxan-2-yl)-cyclohexanone

HRID 2249898Notes

Reaction equation

HRID 2249898 reaction equation
[CH3:1][C:2]1([CH:10]2[CH2:15][CH2:14][CH:13]([OH:16])[CH2:12][CH2:11]2)[O:7][CH2:6][C:5]([CH3:9])([CH3:8])[CH2:4][O:3]1.C[N+]1([O-])CCOCC1.[O-]S([O-])(=S)=O.[Na+].[Na+]>CC#N.CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O>[CH3:1][C:2]1([CH:10]2[CH2:15][CH2:14][C:13](=[O:16])[CH2:12][CH2:11]2)[O:3][CH2:4][C:5]([CH3:8])([CH3:9])[CH2:6][O:7]1

Participants

6

Reactant 3

HCID 24477Sodium ThiosulfateHCID 82029Methyl morpholine oxideHCID 231479574-(2,5,5-Trimethyl-[1,3]dioxan-2-yl)-cyclohexanol

Product 1

HCID 231479474-(2,5,5-Trimethyl-[1,3]dioxan-2-yl)-cyclohexanoneYield 85%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

TPAP (161 mg, 0.05 eq.) was added to a solution of 4-(2,5,5-trimethyl-[1,3]dioxan-2-yl)-cyclohexanol (2.22 g, 1 eq.) and NMO (2.28 g, 2 eq.) in MeCN (65 mL). The reaction mixture was stirred at room temperature overnight. Saturated aqueous solution of Na2S2O3 was added to the mixture and the resulting mixture was stirred vigorously for 15 minutes. The separated aqueous phase was extracted with CH2Cl2. The combined organic layer was dried over Na2SO4, filtered through Celite and concentrated. The crude product was purified by silica gel column chromatography (25% to 50% EtOAc/hexanes) to give 4-(2,5,5-trimethyl-[1,3]dioxan-2-yl)-cyclohexanone (1.87 g, 85%).

Workup

  1. stirringthe resulting mixture was stirred vigorously for 15 minutes
  2. extractionThe separated aqueous phase was extracted with CH2Cl2
  3. dry with materialThe combined organic layer was dried over Na2SO4
  4. filtrationfiltered through Celite
  5. concentrationconcentrated
  6. customThe crude product was purified by silica gel column chromatography (25% to 50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-f1ee43785d28423b9951bec719b86e74
Source dataset
uspto-grants-2008_01
Patent number
US07314936B2

Reaction notes

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