Pyridine → 1,3-Dioxan-5-yl acetate
Reaction equation
[CH2:1]1[O:5][CH2:4][O:3][CH:2]1[CH2:6][OH:7].N1C=CC=CC=1.[C:14](OC(=O)C)(=[O:16])[CH3:15]>>[C:14]([O:7][CH:6]1[CH2:2][O:3][CH2:4][O:5][CH2:1]1)(=[O:16])[CH3:15]Participants
Procedure
A mixture of 10.0 g (96 mmole) of glycerol formal, 8.35 g (105 mmole) of pyridine, and 20 ml of acetic anhydride was stirred at ambient temperature under protection from moisture. After a period ranging from a few hours to 5 days, the solution was fractionally distilled under vacuum. The early fractions consisted primarily of pyridine, acetic acid, and acetic anhydride. The bulk of the product distilled at 56°-57° (1.1 mm). The product fractions (10.8 g) were separated into the 5- and 6-membered ring isomers by preparative HPLC on silica gel in 3:1 hexane-ethyl acetate with recycling. Fractions were identified and checked for purity by analytical HPLC. In total 3.19 g (23%) of 1,3-dioxolane-4-methyl acetate (shorter retention time) and 5.23 g (37%) of 1,3-dioxan-5-yl acetate (longer retention time) were obtained. The structures were confirmed by NMR.
Workup
- waitAfter a period ranging from a few hours to 5 days
- distillationthe solution was fractionally distilled under vacuum
- distillationThe bulk of the product distilled at 56°-57° (1.1 mm)
- customThe product fractions (10.8 g) were separated into the 5- and 6-membered ring isomers by preparative HPLC on silica gel in 3:1 hexane-ethyl acetate with recycling
Sources & evidence
- ORD record
- ord-dd8be7b7069d4c87bcde73e29d65278e
- Source dataset
- uspto-grants-1989_03
- Patent number
- US04816447
Reaction notes
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