Reaction equation
[I:1]I.[CH2:3]([CH:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:12]O)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.[O-]S([O-])=O.[Na+].[Na+]>ClCCl>[I:1][CH2:12][CH:11]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
Iodine (12.25 g, 48.3 mmol) was added to a solution of 2-octyl-1-dodecanol (12.42 g, 41.6 mmol), triphenylphosphine (13.17 g, 50.2 mmol), and imidazole (3.42 g, 50.2 mmol) in 80 mL dichloromethane at 0° C. After stirring for 30 minutes, the reaction mixture was allowed to warm to room temperature over 4 hours before 12 mL of saturated Na2SO3 (aq) was added. The organics were concentrated by evaporation and the mixture taken up in 500 mL pentane, washed three times with 200 mL water, and once with 150 mL brine. The mixture was then passed through a 3 cm silica gel plug, and dried over Na2SO4. The organics were concentrated by evaporation to give a colorless oil (15.78 g, yield 92.9%). 1H NMR (CDCl3 500 MHz): δ: 2.60 (d, J=5.0 Hz, 2H), 2.00 (t, J=5.0 Hz, 1H), 1.30-1.20 (b, 32H), 0.89 (t, J=7.5 Hz, 6H); MS (EI): m/z (%) 408.23 (100) [M+]. Elemental Analysis (calc. C, 58.81; H, 10.12): found C, 58.70; H, 9.97.
Workup
- additionwas added
- concentrationThe organics were concentrated by evaporation
- washwashed three times with 200 mL water
- dry with materialdried over Na2SO4
- concentrationThe organics were concentrated by evaporation
Sources & evidence
- ORD record
- ord-3824af1174994d87889bc1a111ee3b6b
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09312492B2
Linked notes
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