Citric Acid → 4-(3-Fluorophenoxy)thiophene-2-carbaldehyde

HRID 2080073Notes

Reaction equation

HRID 2080073 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)[O:5][C:6]1[CH:7]=[C:8]([CH:11]2OCC[O:12]2)[S:9][CH:10]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O.C(=O)(O)[O-].[Na+]>CO>[F:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)[O:5][C:6]1[CH:7]=[C:8]([CH:11]=[O:12])[S:9][CH:10]=1

Participants

5

Reactant 3

HCID 311Citric AcidHCID 516892Sodium BicarbonateHCID 231305304-(3-Fluoro-phenoxy)-thiophen-2-yl-[1,3]dioxolane

Product 1

HCID 231306054-(3-Fluorophenoxy)thiophene-2-carbaldehydeYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-(4-(3-fluoro-phenoxy)-thiophen-2-yl)-[1,3]dioxolane described in Preparation Example 33 (280 mg, 1.05 mmol) in methanol (10 mL) was added citric acid aqueous solution (10 mL), and the solution was stirred at room temperature for 30 minutes. The reaction solution was neutralized with an aqueous solution of sodium bicarbonate, the solution was extracted with ethyl acetate, the organic layer was dried over anhydrous sodium sulfate, the solvent was evaporated in vacuo, and the title compound (210 mg, 0.95 mmol, 90%) was obtained as a colorless oil.

Workup

  1. extractionthe solution was extracted with ethyl acetate
  2. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  3. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-abacad60bb2140cc81806a8dd9e45a01
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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