Triethylamine → 7-Methanesulfonyl-1-heptene
Reaction equation
[CH2:1](N1C(=O)C2N(C)C=NC=2N(C)C1=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]=[CH2:7].C(O)CCCCC=C.[CH3:29][S:30](Cl)(=[O:32])=[O:31].C(N(CC)CC)C>ClCCl.O>[CH3:29][S:30]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]=[CH2:7])(=[O:32])=[O:31]Participants
7
Conditions
- Temperature
- 0 °C
Procedure
This example illustrates the synthesis of 1-(6-Heptenyl)-3,7-dimethylxanthine (CT1534). To a solution of 6-hepten-1-ol (6.00 g, 52.6 mmol) in dichloromethane (120 ml) at 0° C. was added methanesulfonyl chloride (6.07 g, 4.0 ml, 53.0 mmol) followed by triethylamine (7.79 g, 77.0 mmol). After stirring for 10 min at 0° C., the reaction was allowed to warm to 25° C. and stirred for 2 hr. The reaction was poured into water (100 ml) and extracted with dichloromethane (2×100 ml). The organic portions were combined, dried (magnesium sulfate), and evaporated to give the 7-methanesulfonyl-1-heptene as a yellow oil (9.30 g, 93%), which was used without further purification.
Workup
- temperatureto warm to 25° C.
- stirringstirred for 2 hr
- extractionextracted with dichloromethane (2×100 ml)
- dry with materialdried (magnesium sulfate)
- customevaporated
Sources & evidence
- ORD record
- ord-dcd05813b4e74913afc606d0833a6f76
- Source dataset
- uspto-grants-1996_05
- Patent number
- US05521315
Reaction notes
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