Dimethyl Sulfoxide → HCID 9856251, compound

HRID 1935980Notes

Reaction equation

HRID 1935980 reaction equation
[O:1]=[C:2]1[CH2:7][C@@H:6]([O:8][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10])[CH2:5][C@H:4](CC([O-])=O)[CH2:3]1.CS(C)=[O:22]>P([O-])([O-])([O-])=O>[OH:22][C@@H:4]1[CH2:5][C@H:6]([O:8][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10])[CH2:7][C:2](=[O:1])[CH2:3]1

Participants

4

Reactant 2

HCID 679Dimethyl SulfoxideHCID 21334998HCID 21334998, compound

Product 1

HCID 9856251HCID 9856251, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 1061PhosphateSolvent

Procedure

3-Oxo-5-(tert.butyldimethylsilyloxy)-(1S, 5S)-cyclohexylacetate (6, 1.2 parts, 4.2 mmol ) was dissolved in DMSO (10 parts) and 0.1 M phosphate buffer (pH 6.5, 90 parts). To the mixture, PLE (0.1 parts) was added and the reaction mixture was stirred for 48 hr at room temperature. It was filtered through ceilite and filtrate was extracted with ethyl acetate (3×100 parts). Organic extracts were combined and washed with brine. Organic layer was dried on anhydrous sodium sulphate and concentrated under vacuum. Residue was chromatographed on silica gel to afford 3-hydroxy-5-(tertbutyldimethylsilyloxy)-(3R,5S)-cyclohexan-1-one 7 (0.77 parts, 75%).

Workup

  1. additionTo the mixture, PLE (0.1 parts) was added
  2. filtrationIt was filtered through ceilite and filtrate
  3. extractionwas extracted with ethyl acetate (3×100 parts)
  4. washwashed with brine
  5. dry with materialOrganic layer was dried on anhydrous sodium sulphate
  6. concentrationconcentrated under vacuum
  7. customResidue was chromatographed on silica gel

Sources & evidence

ORD record
ord-d3a7c03e1a094f02ac539d81fd4c3759
Source dataset
uspto-grants-2002_05
Patent number
US06388097B1

Reaction notes

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