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Water → HCID 19096637, compound

HRID 486847
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Reaction equation

HRID 486847 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([CH3:38])[O:31][C:30](=[O:32])[C:29]([CH2:33][CH2:34][C:35](=[O:37])[CH3:36])=[CH:28][O:27]1>C(OCC)(=O)C>[CH3:38][C:26]1([CH3:25])[O:31][C:30](=[O:32])[C:29]([CH2:33][CH2:34][CH:35]([OH:37])[CH3:36])=[CH:28][O:27]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 5988Sucrose2×HCID 190966312,2-Dimethyl-5-(3-oxobutyl)-1,3-dioxin-4-one

Product 1

HCID 19096637HCID 19096637, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

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, 350 mg of 2,2-dimethyl-5-(3-oxobutyl)-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 residue was then subjected to column chromatography (an eluent of hexane:ethyl acetate=4:1), thereby obtaining 161 mg (yield 55%) of (-)-2,2-dimethyl-5-(3-hydroxybutyl)-1,3-dioxin-4-one [a compound having the formula (1) in which n is 2, X is a hydrogen atom, Y is a hydrogen atom, and a substituent is present at the 5-position].

Workup

  1. stirringthe solution was then stirred overnight at the same temperature
  2. stirringby stirring overnight
  3. distillationWater of the reaction solution was then distilled off under reduced pressure
  4. extractionthe resultant residue was extracted with dichloromethane
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationAfterward, the solvent was distilled off

Sources & evidence

ORD record
ord-7df38648450a46f09a98fae588ffe1a8
Source dataset
uspto-grants-1994_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05292891

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes