Water → HCID 19972408, compound

HRID 2259867Notes

Reaction equation

HRID 2259867 reaction equation
[Na].[Cl:2][CH2:3][C:4]1[C:13]2[O:12][C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[C:10]([CH3:20])[C:9](=[O:21])[C:8]=2[CH:7]=[CH:6][CH:5]=1.O.[O:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1>C1(C)C(C)=CC=CC=1.C(O)CO>[Cl:2][CH2:3][C:4]1[C:13]2[O:12][C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[C:10]([CH3:20])[C:9](=[O:21])[C:8]=2[CH:7]=[CH:6][CH:5]=1.[OH:23][CH2:28][CH2:27][O:26][CH2:25][C:24]1[C:13]2[O:12][C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[C:10]([CH3:20])[C:9](=[O:21])[C:8]=2[CH:7]=[CH:6][CH:5]=1

Participants

8

Reactant 4

HCID 962WaterHCID 312751,4-DioxaneHCID 5360545SodiumHCID 19972408HCID 19972408, compound

Product 2

HCID 19972408HCID 19972408, compoundHCID 19972532HCID 19972532, compound

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 7237O-XyleneSolvent

Procedure

A solution of 2.5 g of Intermediate XIX in 25 ml of xylene and 3 ml of dioxane was prepared. 0.15 g of sodium was dissolved in 3.10 ml of anhydrous ethylene glycol, and this solution was added dropwise at ambient temperature to the solution of Intermediate XIX. After refluxing for 5.5 hours, the reaction mixture was cooled to ambient temperature and poured into 50 ml of water. It was extracted with dichloromethane, and the extract was washed with sodium chloride solution, dried on anhydrous sodium sulfate and evaporated to dryness in vacuo. The solid residue was crystallized from ethanol, giving 2.1 g of the title compound, m.p. 132°-133° C.

Workup

  1. temperatureAfter refluxing for 5.5 hours
  2. extractionIt was extracted with dichloromethane
  3. washthe extract was washed with sodium chloride solution
  4. dry with materialdried on anhydrous sodium sulfate
  5. customevaporated to dryness in vacuo
  6. customThe solid residue was crystallized from ethanol

Sources & evidence

ORD record
ord-0768f9f4ffe44e03887995590f425f7a
Source dataset
uspto-grants-1995_12
Patent number
US05474994

Reaction notes

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