Hexane → (S)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)prop-1-ene-2-sulfonyl chloride
Reaction equation
C([Li])(C)(C)C.CCCCCC.I[C:13](=[CH2:22])[CH2:14][C@H:15]1[CH2:19][O:18][C:17]([CH3:21])([CH3:20])[O:16]1.[S:23](Cl)([Cl:26])(=[O:25])=[O:24]>C(OCC)C>[CH3:20][C:17]1([CH3:21])[O:16][C@@H:15]([CH2:14][C:13]([S:23]([Cl:26])(=[O:25])=[O:24])=[CH2:22])[CH2:19][O:18]1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
A solution of tert-butyl lithium in hexane (1.7M, 2 eq) is added dropwise to a solution of (S)-4-(2-iodoallyl)-2,2-dimethyl-1,3-dioxolane (1 eq) in diethyl ether at −78° C., and the reaction stirred at −78° C. for 30 min. Sulfuryl dichloride (1 eq) is added, the mixture warmed to room temperature and the solvents removed under reduced pressure.
Workup
- temperaturethe mixture warmed to room temperature
- customthe solvents removed under reduced pressure
Sources & evidence
- ORD record
- ord-a2fd20f564be4e7f911d8f9e03821a81
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08884058B2
Reaction notes
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