4-Toluenesulfonyl chloride → (5Z,8Z,11Z,14Z)-Icosa-5,8,11,14-tetraenyl-4-methylbenzenesulfonate
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].[C:22]1([CH3:32])[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1>N1C=CC=CC=1>[CH2:1]([O:21][S:28]([C:25]1[CH:26]=[CH:27][C:22]([CH3:32])=[CH:23][CH:24]=1)(=[O:30])=[O:29])[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]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
(5Z,8Z,11Z,14Z)-Icosa-5,8,11,14-tetraen-1-ol (0.58 g, 1.997 mmol) was dissolved in pyridine (8 mL) and to this solution p-toluenesulfonyl chloride (0.762 g, 3.99 mmol) was added at 0° C. (ice-bath) and the reaction mixture was stirred under nitrogen for 4 h as the temperature was slowly allowed to rise to room temperature. The solvent was then removed under reduced pressure and the crude was purified on silica gel column chromatography using 5%-10% ethyl/hexane giving the title product as a clear oil (0.551 g, 62%). 1H NMR (CDCl3): δ 7.79 (d, 2H, J=8.2 Hz), δ 7.34 (d, 2H, J=8.2 Hz), 5.35 (m, 8H), 4.02 (t, 2H, J=6.4 Hz), 2.79 (m, 6H), 2.44 (s, 3H), 2.03 (m, 4H), 1.64 (m, 2H), 1.43-1.25 (m, 8H), 1.04 (t, 3H, J=6.8 Hz). m/z (ESI) 467.27 (M++Na).
Workup
- additionwas added at 0° C. (ice-bath)
- customto rise to room temperature
- customThe solvent was then removed under reduced pressure
- customthe crude was purified on silica gel column chromatography
Sources & evidence
- ORD record
- ord-1845d3186b214072ac3abc8d5a42670c
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08563760B2
Reaction notes
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