Potassium Carbonate → HCID 22951115, compound

HRID 480217Notes

Reaction equation

HRID 480217 reaction equation
C([O:9][C@@H:10]1[CH2:18][C@@H:13]2[O:14][C:15](=[O:17])[CH2:16][C@@H:12]2[C@@H:11]1[CH2:19][O:20][Si:21]([C:34]([CH3:37])([CH3:36])[CH3:35])([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=O)C1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+]>CO.[Cl-].[Na+].O>[O:20]([CH2:19][C@H:11]1[C@@H:12]2[C@@H:13]([O:14][C:15](=[O:17])[CH2:16]2)[CH2:18][C@H:10]1[OH:9])[Si:21]([C:34]([CH3:35])([CH3:36])[CH3:37])([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 22951116(3aR,4R,5R,6aS)-5-Benzoyloxy-4-[(t-butyldiphenylsiloxy)methyl]hexahydro-2H-cyclopenta[b]furan-2-one

Product 1

HCID 22951115HCID 22951115, compoundYield 80.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 3 (15.7 g, 30.0 mmol) in methanol (100 mL) was added potassium carbonate (4.14 g, 30.0 mmol). After 1 h, saturated ammonium chloride (100 mL) and saturated brine (100 mL) were added, the mixture was extracted with methylene chloride (3×100 mL), dried (magnesium sulfate), filtered, concentrated, and chromatographed on a 15 cm tall×41 mm diameter silica gel column eluting with 40% ethyl acetate in hexane to afford 4 (9.93 g, 79%).

Workup

  1. extractionthe mixture was extracted with methylene chloride (3×100 mL)
  2. dry with materialdried (magnesium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customchromatographed on a 15 cm tall×41 mm diameter silica gel column
  6. washeluting with 40% ethyl acetate in hexane

Sources & evidence

ORD record
ord-df13140665f3403ca22c7af5081f8c87
Source dataset
uspto-grants-2003_11
Patent number
US06649655B2

Reaction notes

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