Citric Acid → HCID 23130410, compound

HRID 2080080Notes

Reaction equation

HRID 2080080 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)[CH2:5][C:6]1[S:10][C:9]([CH:11]2OCC[O:12]2)=[CH:8][CH:7]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O.C(=O)(O)[O-].[Na+].C(OCC)(=O)C>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)[CH2:5][C:6]1[S:10][C:9]([CH:11]=[O:12])=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 311Citric AcidHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 23130459HCID 23130459, compound

Product 1

HCID 23130410HCID 23130410, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-(5-(3-chloro-benzyl)-thiophen-2-yl)-[1,3]dioxolane described in Preparation Example 43 (1.6 g, 5.7 mmol) in methanol (20 mL) was added citric acid aqueous solution (20 mL), and the solution was stirred at room temperature for 20 minutes. An aqueous solution of sodium bicarbonate and ethyl acetate were added to the reaction solution, which was then partitioned, the organic layer was washed with water twice and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the title compound (1.2 g, 5.08 mmol, 89.2%) was obtained as a yellow oil.

Workup

  1. customwas then partitioned
  2. washthe organic layer was washed with water twice
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-9b8fa6d8d776411d84a123b89c757310
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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