Reaction equation
[CH3:1][C:2]([CH3:4])=[O:3].O[CH2:6][C:7]([C@H:9]([C@@H:11]([C@H:13]([CH2:15][OH:16])[OH:14])[OH:12])[OH:10])=[O:8].I.N1C=C[CH:21]=[CH:20][CH:19]=1>>[CH3:1][C:2]1([CH3:4])[O:10][C@H:9]2[C@@H:11]3[O:12][C:20]([CH3:21])([CH3:19])[O:14][C@:13]3([CH2:15][OH:16])[O:8][C@H:7]2[CH2:6][O:3]1Participants
Conditions
- Temperature
- 60 °C
Procedure
To 200 ml of acetone were added 10.0 g of L-sorbose and 223 mg of hydriodic acid (57%) and the mixture was refluxed with stirring in a water bath at 60° C. for 6 hours. During this reaction, the refluxing solvent was dried with 20 g of Molecular Sieves 3A interposed between the reaction vessel and the cooling jacket. After completion of the reaction, a small amount of pyridine was added. The acetone was then distilled off under reduced pressure and the residue was dissolved in benzene. The benzene solution was washed with aqueous sodium bicarbonate and water and dried over anhydrous magnesium sulfate. The benzene was distilled off under reduced pressure to give 12.13 g (84.0%) of 2,3:4,6-di-O-isopropylidene-L-sorbofuranose (purity ≥98%). Melting point: 77°-78° C. (recrystallized from petroleum ether).
Workup
- temperaturethe mixture was refluxed
- customDuring this reaction
- dry with materialthe refluxing solvent was dried with 20 g of Molecular Sieves 3A
- customAfter completion of the reaction
- distillationThe acetone was then distilled off under reduced pressure
- dissolutionthe residue was dissolved in benzene
- washThe benzene solution was washed with aqueous sodium bicarbonate and water
- dry with materialdried over anhydrous magnesium sulfate
- distillationThe benzene was distilled off under reduced pressure
Sources & evidence
- ORD record
- ord-61169ec443be4360ba80f9006bf3a286
- Source dataset
- uspto-grants-1984_08
- Patent number
- US04464530
Linked notes
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