Citric Acid → 5-(4-Fluorobenzyl)furan-2-carbaldehyde

HRID 78245Notes

Reaction equation

HRID 78245 reaction equation
[F:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][C:7]2[O:11][C:10]([CH:12]3OCC[O:13]3)=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO>[F:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][C:7]2[O:11][C:10]([CH:12]=[O:13])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 311Citric AcidHCID 592550712-(5-(4-Fluoro-benzyl)-furan-2-yl)-[1,3]dioxolane

Product 1

HCID 592551775-(4-Fluorobenzyl)furan-2-carbaldehydeYield 121.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a methanol (45 mL) solution of 2-(5-(4-fluoro-benzyl)-furan-2-yl)-[1,3]dioxolane (4.51 g, 18.2 mmol) described in Manufacturing Example 208-1-1 was added a solution (45 mL) of citric acid (12.2 g, 63.7 mmol), which was vigorously stirred for 1 hour at room temperature. This mixture was partitioned into ethyl acetate and water. The organic layer was separated, washed with a saturated sodium hydrogencarbonate aqueous solution, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure to obtain the title compound (4.51 g, 51%). The title compound was used in the following reaction without any further purification.

Workup

  1. customThis mixture was partitioned into ethyl acetate and water
  2. customThe organic layer was separated
  3. washwashed with a saturated sodium hydrogencarbonate aqueous solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-7e3840910fe542c7aa521d20d53db15e
Source dataset
uspto-grants-2014_09
Patent number
US08841327B2

Reaction notes

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