Acetone → HCID 54180510, compound

HRID 894105Notes

Reaction equation

HRID 894105 reaction equation
[N+:1]([C:4]1[CH:43]=[CH:42][C:7]([C:8]([O:10][C@@H:11]2[C@H:15]([O:16][C:17](=[O:27])[C:18]3[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=3)[C@@H:14]([CH2:28][O:29][C:30](=[O:40])[C:31]3[CH:36]=[CH:35][C:34]([N+:37]([O-:39])=[O:38])=[CH:33][CH:32]=3)[O:13][C@H:12]2Br)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].C1C=CC=CC=1.CC(C)=[O:52]>ClCCl.O.C(=O)([O-])[O-].[Ag+2]>[N+:1]([C:4]1[CH:43]=[CH:42][C:7]([C:8]([O:10][C@@H:11]2[C@H:15]([O:16][C:17](=[O:27])[C:18]3[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=3)[C@@H:14]([CH2:28][O:29][C:30](=[O:40])[C:31]3[CH:36]=[CH:35][C:34]([N+:37]([O-:39])=[O:38])=[CH:33][CH:32]=3)[O:13][CH:12]2[OH:52])=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

7

Reactant 3

HCID 180AcetoneHCID 241BenzeneHCID 53819978HCID 53819978, compound

Product 1

HCID 54180510HCID 54180510, compoundYield 65%

Reagents, catalysts & solvents 3

HCID 178418647HCID 178418647, compoundCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
5 °C

Procedure

3 g of 2,3,5-tri-O-(p-nitrobenzoyl)-β-D-ribofuranosyl bromide prepared by the procedure described in Example 2 were dissolved in a mixture of 25 ml of acetone and 25 ml of dichloromethane. This solution was cooled to 5° C. and treated with a suspension of silver carbonate (1.25 g) in water (5 ml) with vigorous stirring. Stirring was continued for 90 minutes while the mixture was maintained at 5° C. The mixture was filtered and the filtrate evaporated under reduced pressure to yield a syrup. This syrup was redissolved in 50 ml of dichloromethane, dried over anhydrous MgSO4 and evaporated to yield a syrup which solidified on slow coevaporation with benzene. This yielded 1.76 g (65% yield) of 2,3,5-tri-O-(p-nitrobenzoyl)-D-ribofuranose. Recrystallization of this product from nitromethane yielded colorless needles which had a melting point of 177° to 178° C.

Workup

  1. temperaturewas maintained at 5° C
  2. filtrationThe mixture was filtered
  3. customthe filtrate evaporated under reduced pressure
  4. customto yield a syrup
  5. dry with materialdried over anhydrous MgSO4
  6. customevaporated
  7. customto yield a syrup which

Sources & evidence

ORD record
ord-6d6d184be479419ba6e240245b25e4dc
Source dataset
uspto-grants-1981_08
Patent number
US04282349

Reaction notes

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