Hydrochloric Acid → 4-[3-(Ethylsulfonyl)propyl]bicyclo[2.2.2]octane-1-carboxylic acid

HRID 605515Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 605515
[CH2:1]([S:3]([CH2:6][CH2:7][CH2:8][C:9]12[CH2:16][CH2:15][C:12]([C:17]([O:19]C)=[O:18])([CH2:13][CH2:14]1)[CH2:11][CH2:10]2)(=[O:5])=[O:4])[CH3:2].[OH-].[K+].Cl>CO.O>[CH2:1]([S:3]([CH2:6][CH2:7][CH2:8][C:9]12[CH2:10][CH2:11][C:12]([C:17]([OH:19])=[O:18])([CH2:13][CH2:14]1)[CH2:15][CH2:16]2)(=[O:5])=[O:4])[CH3:2]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 22591697Methyl 4-[3-(ethylsulfonyl)propyl]bicyclo[2.2.2]octane-1-carboxylate

Produkt 1

HCID 225916994-[3-(Ethylsulfonyl)propyl]bicyclo[2.2.2]octane-1-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 22242641Methanol--water (1/1)Lösungsmittel

Versuchsvorschrift

Sulfone 2-7 (3.1 g, 10 mmol) was dissolved in 9:1 MeOH/water (50 mL) and treated with potassium hydroxide (3 g). The solution was stirred at room temperature overnight, then the mixture was acidified with 1 N HCl and extracted four times with 50 mL of methylene chloride. The organic layer was dried over anhydrous sodium sulfate and evaporated to afford 4-[3-(ethylsulfonyl)propyl]bicyclo[2.2.2]octane-1-carboxylic acid (2-8) which was used without purification in the next step. 1H NMR (500 MHz, CDCl3): δ 3.03 (2H, q, J=7 Hz), 2.94 (2H, dd, J=7.5 Hz), 1.84 (8H, m), 1.45 (8H, m), 1.30 (2H, m) ppm.

Aufarbeitung

  1. extractionextracted four times with 50 mL of methylene chloride
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-e65c37ab126143b4a96d7af11c06aab1
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07915252B2

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