Water → HCID 14559529, compound

HRID 1657205Notes

Reaction equation

C(O)[C@H]1O[C@H](O[C@]2(CO)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@@H]1O.O.[CH3:25][C:26]1([CH3:39])[O:31][C:30](=[O:32])[CH:29]=[C:28]([CH2:33][CH2:34][CH2:35][C:36](=[O:38])[CH3:37])[O:27]1>C(OCC)(=O)C>[CH3:39][C:26]1([CH3:25])[O:31][C:30](=[O:32])[CH:29]=[C:28]([CH2:33][CH2:34][CH2:35][CH:36]([OH:38])[CH3:37])[O:27]1

Participants

Conditions

Temperature: 32 °C

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, and the solution was then stirred at 32° C. for 30 minutes. Afterward, 300 mg of 2,2-dimethyl-6-(4-oxopentyl)-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 resultant residue was extracted with dichloromethane and then dried over anhydrous sodium sulfate. Afterward, the solvent was distilled off, and the resultant residue wa then subjected to column chromatography (an eluent of hexane:ethyl acetate=4:1), thereby obtaining 148 mg (yield 50%) of (-)-2,2-dimethyl-6-(4-hydroxypentyl)-1,3-dioxin-4-one [a compound having the formula (1) in which n is 3, X is a hydrogen atom, Y is the 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 resultant residue was extracted with dichloromethane
dry with materialdried over anhydrous sodium sulfate
distillationAfterward, the solvent was distilled off

Sources & evidence

ORD record: ord-78536218e60e490a8efb0dbc2b42a3e0
Source dataset: uspto-grants-1993_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05256800

Reaction notes

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