Iodine → 16-Heptadecenyl chloride
Reaction equation
[Mg].II.[CH2:4](Br)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:13]=[CH2:14].Br[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][Cl:23].S(=O)(=O)(O)O>C1COCC1.[Cu](I)I>[CH2:22]([Cl:23])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH:5]=[CH2:4]Participants
Procedure
This example illustrates a synthesis of 1-(16,17-Oxidoheptadecyl)-3,7-dimethylxanthine (inventive compound no. 3516). To a suspension of magnesium (3.10 g, 129 mmol) and a crystal of iodine in THF (10 mL) was added 10-undecenyl bromide (6.00 g, 25.8 mmol, available from MTM) in THF (20 mL) over 40 minutes and the reaction stirred for a further 30 minutes after the addition was complete. The solution was added via a canula over 50 minutes to a suspension of copper iodide (0.50 g, 2.58 mmol) and 1-bromo-6-chloro hexane (6.00 mL, 40.0 mmol) in THF (20 mL) and stirred at 25° C. for 16 hours. Sulfuric acid (1.0M, 50 mL) was added, extracted with diethyl ether (2×60 mL) and the organic solvent dried using magnesium sulfate and the solvent subsequently evaporated. The residue was distilled at 0.75 mmHg to yield 1.78 g (25% yield, b.p. 130°-135° C.) 16-heptadecenyl chloride as a colourless liquid.
Workup
- additionafter the addition
- stirringstirred at 25° C. for 16 hours
- extractionextracted with diethyl ether (2×60 mL)
- customthe organic solvent dried
- customthe solvent subsequently evaporated
- distillationThe residue was distilled at 0.75 mmHg
Sources & evidence
- ORD record
- ord-b40bdeabb30e4a539d4aa559747bc7b2
- Source dataset
- uspto-grants-1999_02
- Patent number
- US05866576
Reaction notes
Loading…