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

HRID 1691351Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1691351
[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

Komponenten

4

Edukt 2

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

Produkt 1

HCID 592551775-(4-Fluorobenzyl)furan-2-carbaldehydeAusbeute 121,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-cf09fbb519744043b922bebb3be6cd43
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08153662B2

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