Water → HCID 15062403, compound
Reaction equation
[CH2:1]([OH:23])[C@H:2]1O[C@H:6]([O:8][C@:9]2(CO)O[C@H:12]([CH2:14]O)[C@@H:11](O)[C@@H:10]2O)[C@H:5]([OH:20])[C@@H:4](O)[C@@H:3]1[OH:22].O.[CH3:25][C:26]1([CH3:44])OC(=O)C=C(CC(=O)CCC2C=CC=CC=2)[O:27]1.[C:45](OCC)(=O)[CH3:46]>>[CH3:25][C:26]1([CH3:44])[O:27][C:1](=[O:23])[CH:2]=[C:3]([CH2:4][CH:5]([OH:20])[CH2:6][O:8][CH2:9][C:10]2[CH:11]=[CH:12][CH:14]=[CH:46][CH:45]=2)[O:22]1Participants
Procedure
30 g of baker's yeast (made by Oriental Yeast Co., Ltd.) and 15 g of saccharose were added in 30 ml of tap water at 32° C., and the solution was then stirred for 30 minutes. Afterward, 300 mg of 2,2-dimethyl-6-(3-benzyl-2-oxopropyl)-1,3-dioxin-4-one were added thereto, and the solution was then stirred overnight at the same temperature. 7.5 g of saccharose were further added thereto, followed by stirring overnight. Water of the reaction solution was then distilled off under reduced pressure, and the residue was extracted with dichloromethane and then dried over anhydrous sodium sulfate. Afterward, the solvent was distilled off, and the residue was then subjected to column chromatography (an eluent of hexane:ethyl acetate=4:1), thereby obtaining 168 mg (yield 56%) of (-)-2,2-dimethyl-6-(3-benzyloxy-2-hydroxypropyl)-1,3-dioxin-4-one [a compound having the formula (1) in which n is 1, X is a benzyloxy group, Y is a hydrogen atom, and a substituent is present at the 6-position].
Workup
- stirringthe solution was then stirred overnight at the same temperature
- stirringby stirring overnight
- distillationWater of the reaction solution was then distilled off under reduced pressure
- extractionthe residue was extracted with dichloromethane
- dry with materialdried over anhydrous sodium sulfate
- distillationAfterward, the solvent was distilled off
Sources & evidence
- ORD record
- ord-b298a8ad3e574f93a00b5a6f8685f65b
- Source dataset
- uspto-grants-1994_03
- Patent number
- US05292891
Reaction notes
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