Potassium Carbonate → HCID 69112481, compound

HRID 2228837Notes

Reaction equation

HRID 2228837 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C@H:8]1[CH2:13][C@H:12]([O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])[CH2:11][C@@H:10](CC([O-])=O)[CH2:9]1.C(=O)([O-])[O-:27].[K+].[K+]>CO>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C@H:8]1[CH2:13][C@H:12]([O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])[CH2:11][C@@H:10]([OH:27])[CH2:9]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 86758332HCID 86758332, compound

Product 1

HCID 69112481HCID 69112481, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-tetrahydro-2H-2-pyranyloxy-5-(tert.butyldimethylsilyloxy)-(1S,3R,5R)-cyclohexylacetate (6, 3.5 parts, 9.16 mmol) was dissolved in dry methanol (25 parts). To the solution anhydrous potassium carbonate (0.828 parts, 6 mmol) was added and the mixture was stirred at room temperature for 2 hr. Methanol was removed under vacuum and residue was extracted several times with dichloromethane. Dichloromethane layers were combined and washed with water followed by brine wash. It was dried on anhydrous sodium sulfate. Solvent was removed under vacuum and residue was purified by flash column chromatography to yield 3-tetrahydro-2H-2-pyranyloxy-5-(tert.butyldimethylsilyloxy)-(1S,3R,5R)-cyclohexan-1-ol (7, yield 3 parts, 96%).

Workup

  1. customMethanol was removed under vacuum and residue
  2. extractionwas extracted several times with dichloromethane
  3. washwashed with water
  4. washwash
  5. dry with materialIt was dried on anhydrous sodium sulfate
  6. customSolvent was removed under vacuum and residue
  7. customwas purified by flash column chromatography

Sources & evidence

ORD record
ord-cf2ea5c85efe431f82112f218757e0b1
Source dataset
uspto-grants-2002_07
Patent number
US06417374B1

Reaction notes

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