Ethanol → Ethyl (1S,3S,6R)-7-oxabicyclo[4.1.0]heptane-3-carboxylate
Reaction equation
I[C@@H:2]1[C@@H:8]2[CH2:9][C@@H:5]([C:6](=[O:10])[O:7]2)[CH2:4][CH2:3]1.[OH-].[Na+].[CH2:13]([OH:15])[CH3:14]>>[CH2:13]([O:15][C:6]([C@H:5]1[CH2:4][CH2:3][C@@H:2]2[C@@H:8]([O:7]2)[CH2:9]1)=[O:10])[CH3:14]Participants
4
Procedure
(1S,4S,5S)-4-Iodo-6-oxabicyclo[3.2.1]octan-7-one (J. Org. Chem., vol. 61, p. 8687 (1996)) (89.3 g) was suspended in ethanol (810 mL), and 2N aqueous sodium hydroxide (213 mL) was added thereto, followed by stirring at room temperature for 3 hours. The solvent was distilled away under reduced pressure, and water was added to the residue. The thus-obtained mixture was extracted with methylene chloride, and the extract was dried over anhydrous magnesium sulfate. The solvent was distilled away under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=17:3), to thereby give the title compound (41.3 g).
Workup
- distillationThe solvent was distilled away under reduced pressure, and water
- additionwas added to the residue
- extractionThe thus-obtained mixture was extracted with methylene chloride
- dry with materialthe extract was dried over anhydrous magnesium sulfate
- distillationThe solvent was distilled away under reduced pressure
- customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=17:3)
Sources & evidence
- ORD record
- ord-57357515c12e46049858aa16995254e1
- Source dataset
- uspto-grants-2009_08
- Patent number
- US07576135B2
Reaction notes
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