Pyridine → 3,5-Dioxohexanoic acid
Reaction equation
CCCCCCCCCCCCC/C=[CH:15]/[C@@H:16]([OH:21])[C@@H:17](N)[CH2:18][OH:19].N1C=CC=CC=1.C([O:31][C:32](=[O:34])[CH3:33])(=O)C>ClCCl.CN(C)C1C=CN=CC=1>[CH3:15][C:16]([CH2:17][C:18]([CH2:33][C:32]([OH:31])=[O:34])=[O:19])=[O:21]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 25 °C
Procedure
To a cooled (0° C.) solution of 38.1 mg (0.127 mmol) of D-erythro-sphingosine 1 in 3.0 mL of dichloromethane was added 61.5 μL (0.762 mmol) of pyridine, 72.0 μL (0.762 mmol) of acetic anhydride and 0.78 mg (6.4 μmol) of 4-dimethylaminopyridine. The solution was warmed to 25° C., stirred for 2 h and poured in 30 mL of dichloromethane. The mixture was washed with 40 mL each of saturated aqueous sodium bicarbonate, saturated aqueous cupric sulfate, brine and dried over anhydrous sodium sulfate. Concentration in vacuo yielded 52.3 mg (97%) of nearly pure triacetate as an off-white solid. Recrystallization from hexanes afforded 48.2 mg (89%) of pure triacetate as feathery white crystals, mp 102-103° C. A second recrystallization from diethyl ether:hexanes gave an analytical sample as feathery white crystals, mp 103.0-103.5° C.
Workup
- washThe mixture was washed with 40 mL each of saturated aqueous sodium bicarbonate, saturated aqueous cupric sulfate, brine
- dry with materialdried over anhydrous sodium sulfate
- concentrationConcentration in vacuo
Sources & evidence
- ORD record
- ord-4c0431411e5e465db7be8334ccab04a9
- Source dataset
- uspto-grants-1991_04
- Patent number
- US05012000
Reaction notes
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