Sodium Bicarbonate → HCID 22607995, compound

HRID 2080105Notes

Reaction equation

HRID 2080105 reaction equation
[C:1]1([S:7][C:8]2[CH:9]=[C:10]([CH:14]3OCC[O:15]3)[CH:11]=[CH:12][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)(O)[O-].[Na+]>C(O)C.O.O1CCCC1.S(=O)(=O)(O)O>[C:1]1([S:7][C:8]2[CH:9]=[C:10]([CH:11]=[CH:12][CH:13]=2)[CH:14]=[O:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 2

HCID 516892Sodium BicarbonateHCID 19421799HCID 19421799, compound

Product 1

HCID 22607995HCID 22607995, compoundYield 98%

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 962WaterSolventHCID 1118Sulfuric AcidSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

2-(3-Phenylsulfanyl-phenyl)-[1,3]dioxolane described in Preparation Example 91 (396 mg, 1.53 mmol) was dissolved in a mixture solution of ethanol (5 mL), water (5 mL), tetrahydrofuran (5 mL) and sulfuric acid (1 mL), and the solution was stirred for 2.5 hours under reflux. The reaction solution was cooled to 0° C., an aqueous solution of saturated sodium bicarbonate was added thereto, the solution was extracted with ethyl acetate, the organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated in vacuo, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1), and the title compound (323 mg, 1.51 mmol, 98%) was obtained as a colorless oil.

Workup

  1. temperatureunder reflux
  2. extractionthe solution was extracted with ethyl acetate
  3. washthe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated in vacuo
  6. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-bc3a4863e7d949dc960214483889e6c6
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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