Carbon Tetrachloride → (2R, 3S)-(-)-3-[8-(methoxyethoxymethoxy)octyl]oxirane-2-carboxylic acid
Reaction equation
ClC(Cl)(Cl)Cl.C(#N)C.[CH3:9][O:10][CH2:11][CH2:12][O:13][CH2:14][O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C@@H:24]1[O:26][C@H:25]1[CH2:27][OH:28].I([O-])(=O)(=O)=[O:30].[Na+]>O.O.O.[Ru](Cl)(Cl)Cl.O>[CH3:9][O:10][CH2:11][CH2:12][O:13][CH2:14][O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C@@H:24]1[O:26][C@H:25]1[C:27]([OH:30])=[O:28]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
2.5 ml of tetrachloromethane, 2.5 ml of acetonitrile, 3.9 ml of water, 1.5 mmol of the alcohol 5, 4.5 mmol of sodium periodate and 5 mol % of ruthenium(III) chloride trihydrate are combined in this sequence, and the mixture is stirred overnight at room temperature. The batch is evaporated, and the residue is taken up in 10 ml of saturated NaCl solution and 8 ml of CH2Cl2. The phases are separated, the aqueous phase is extracted with CH2Cl2, the combined organic phases are washed with saturated NaCl solution and dried over MgSO4, and the solvent is removed in vacuo. The oxiranecarboxylic acid obtained is employed without further purification.
Workup
- customThe batch is evaporated
- customThe phases are separated
- extractionthe aqueous phase is extracted with CH2Cl2
- washthe combined organic phases are washed with saturated NaCl solution
- dry with materialdried over MgSO4
- customthe solvent is removed in vacuo
Sources & evidence
- ORD record
- ord-2203184a533e4f44b58cbcbb88fd81ea
- Source dataset
- uspto-grants-1994_08
- Patent number
- US05336436
Reaction notes
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