Acetone → HCID 178461615, compound

HRID 2057567

Reaction equation

HRID 2057567 reaction equation
[CH3:1][C@@H:2]1[O:7][C@@H:6]([O:8][CH2:9][C@H:10]2[O:15][C@@H:14]([O:16][C:17]3[C:26](=[O:27])[C:25]4[C:24]([OH:28])=[CH:23][C:22]([OH:29])=[CH:21][C:20]=4[O:19][C:18]=3[C:30]3[CH:31]=[CH:32][C:33]([OH:37])=[C:34]([OH:36])[CH:35]=3)[C@H:13]([OH:38])[C@@H:12]([OH:39])[C@@H:11]2[OH:40])[C@H:5]([OH:41])[C@H:4]([OH:42])[C@H:3]1[OH:43].[CH3:44][C:45]([CH3:47])=[O:46].ClC(OC)=O>CN(C)C=O>[CH3:1][C@@H:2]1[O:7][C@@H:6]([O:8][CH2:9][C@H:10]2[O:15][C@@H:14]([O:16][C:17]3[C:26](=[O:27])[C:25]4[C:24]([OH:28])=[CH:23][C:22]([OH:29])=[CH:21][C:20]=4[O:19][C:18]=3[C:30]3[CH:31]=[CH:32][C:33]([OH:37])=[C:34]([OH:36])[CH:35]=3)[C@H:13]([OH:38])[C@@H:12]([OH:39])[C@@H:11]2[OH:40])[C@H:5]([OH:41])[C@H:4]([OH:42])[C@H:3]1[OH:43].[CH2-:44][C:45]([CH3:47])=[O:46]

Participants

5

Reactant 3

HCID 180AcetoneHCID 6586Methyl chloroformateHCID 5280805Rutin

Product 1

HCID 178461615HCID 178461615, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

15 grams of rutin are dissolved in 60 cc of dimethylformamide. After addition of 100 cc of acetone, 15 cc of methyl chloroformate are added dropwise while agitating the mixture. Since the reaction is exothermic, the mixture is maintained at ambient temperature with cooling. At the end of 6 hours, the mixture is evaporated under vacuum. The residue is taken up in 500 cc of water. The solution is extracted with ether. The residual aqueous phase is extracted with ethyl acetate. After evaporation of the organic phase, about 10 grams of rutin acetonide is obtained, which can then be recrystallized.

Workup

  1. additionare added dropwise
  2. temperaturewith cooling
  3. customAt the end of 6 hours, the mixture is evaporated under vacuum
  4. extractionThe solution is extracted with ether
  5. extractionThe residual aqueous phase is extracted with ethyl acetate
  6. customAfter evaporation of the organic phase

Sources & evidence

ORD record
ord-12f4f7814d3b45ec9f93baa466eef585
Source dataset
uspto-grants-1980_07
Patent number
US04211772

Linked notes

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