Water → Arachidonyl methane sulfonate

HRID 1861238Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1861238
[CH2:1]([OH:21])[CH2:2][CH2:3][CH2:4]/[CH:5]=[CH:6]\[CH2:7]/[CH:8]=[CH:9]\[CH2:10]/[CH:11]=[CH:12]\[CH2:13]/[CH:14]=[CH:15]\[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].[CH3:22][S:23](Cl)(=[O:25])=[O:24].O.CCOCC>N1C=CC=CC=1>[CH3:22][S:23]([O:21][CH2:1][CH2:2][CH2:3][CH2:4]/[CH:5]=[CH:6]\[CH2:7]/[CH:8]=[CH:9]\[CH2:10]/[CH:11]=[CH:12]\[CH2:13]/[CH:14]=[CH:15]\[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])(=[O:25])=[O:24]

Komponenten

6

Edukt 4

HCID 962WaterHCID 3283Diethyl EtherHCID 31297Methanesulfonyl chlorideHCID 10891603Arachidonyl alcohol

Produkt 1

HCID 11122179Arachidonyl methane sulfonateAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

Arachidonyl alcohol (0.34 mmol, 100 mg) in dry pyridine (5 ml) was cooled to 0° C. Methane sulfonyl chloride (0.52 mmol; 40 mg) was added to the above solution under a nitrogen atmosphere. The reaction mixture was slowly brought to room temperature at which the reaction was continued for 5 hours. Water (20 ml) and ether (20 ml) were then added to the reaction mixture after which the organic phase was separated, washed with 2N sulfuric acid, then with water and then with a 10% solution of potassium carbonate. The reaction mixture was dried by evaporation of the solvents to obtain an the oily product arachidonyl methane sulfonate, (75 mg; yield 59%) exhibiting the following: 1H HMR (CDCl3) δ 5.34-5.41 (m, 8H), 4.23 (t, J=6.6 Hz, 2H), 3.00 (s, 3H), 2.75-2.84 (m, 6H), 2.04-2.12 (m, 4H), 1.65-1.74 (m, 2H), 1.33-1.50 (m, 2H), 1.25-.130 (m, 6H), 0.89 (t, J=7.2 Hz, 3H). IR (cm−1): 2900, 2850, 1350, 1170, 940.

Aufarbeitung

  1. customwas slowly brought to room temperature at which
  2. customwas separated
  3. washwashed with 2N sulfuric acid
  4. customThe reaction mixture was dried by evaporation of the solvents

Quellen und Nachweise

ORD-Eintrag
ord-582dcfcb90bc4a83b34c174a5e26baf0
Quelldatensatz
uspto-grants-2003_03
Patentnummer
US06531636B1

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