Water → HCID 70022905, compound

HRID 989616Notes

Reaction equation

HRID 989616 reaction equation
C([O:4][C@H:5]1[CH2:10][CH2:9][C@H:8]2[C:11]3[C@H:20]([CH2:21][CH2:22][C@:6]12[CH3:7])[C:19]1[CH2:18][CH2:17][CH:16]([O:23][Si:24]([C:37]([CH3:40])([CH3:39])[CH3:38])([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:15][C:14]=1[CH2:13][CH:12]=3)(=O)C.C(=O)([O-])[O-].[K+].[K+].O>CO.ClCCl>[Si:24]([O:23][CH:16]1[CH2:17][CH2:18][C:19]2[C@@H:20]3[C:11]([C@H:8]4[C@@:6]([CH2:22][CH2:21]3)([CH3:7])[C@@H:5]([OH:4])[CH2:10][CH2:9]4)=[CH:12][CH2:13][C:14]=2[CH2:15]1)([C:37]([CH3:40])([CH3:39])[CH3:38])([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

6

Reactant 3

HCID 962WaterHCID 11430Potassium Carbonate3×HCID 70022690HCID 70022690, compound

Product 1

HCID 70022905HCID 70022905, compoundYield 65.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To the acetates 11 (2.2 g, 4.0 mmol) in a mixture of methanol (60 mL) and dichloromethane (10 mL) was added potassium carbonate (0.1 eq, 55 mg, 0.4 mmol). After stirring for 4 h an additional portion of potassium carbonate (1.0 eq, 0.55 g, 4.0 mmol) was added. The mixture was stirred 16 h and more potassium carbonate (1.0 eq, 0.55 g, 4.0 mmol) was added. After 24 h water (100 mL) was added, the layers were separated and the aqueous layer was extracted with dichloromethane (3×100 mL). The organic layers were combined, washed with saturated aqueous NaCl solution (100 mL), dried over magnesium sulfate and concentrated under reduced pressure to give an oil that was purified by flash column chromatography on silica gel eluting with 20% EtOAc/hexane to give the alcohols 12 (1.34 g), Rf0.5 (30% EtOAc/hexane), as a white foam which was used directly.

Workup

  1. additionwas added
  2. customthe layers were separated
  3. extractionthe aqueous layer was extracted with dichloromethane (3×100 mL)
  4. washwashed with saturated aqueous NaCl solution (100 mL)
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto give an oil that
  8. customwas purified by flash column chromatography on silica gel eluting with 20% EtOAc/hexane

Sources & evidence

ORD record
ord-6325068cf7814dd289d7e912df6d3089
Source dataset
uspto-grants-2002_10
Patent number
US06458778B1

Reaction notes

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