Water → Arachidonyl methane sulfonate
Reaction equation
[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]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
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.
Workup
- customwas slowly brought to room temperature at which
- customwas separated
- washwashed with 2N sulfuric acid
- customThe reaction mixture was dried by evaporation of the solvents
Sources & evidence
- ORD record
- ord-582dcfcb90bc4a83b34c174a5e26baf0
- Source dataset
- uspto-grants-2003_03
- Patent number
- US06531636B1
Reaction notes
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