Water → HCID 21710592, compound

HRID 650991Notes

Reaction equation

HRID 650991 reaction equation
[O:1]1CCC[O:3][CH:2]1[CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]1[O:20][N:19]=[C:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:17]=1.C(O)(C)C.ClCCl.O>CC(C)=O.[O-2].[Cr+6].[O-2].[O-2].S(=O)(=O)(O)O>[C:2]([CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]1[O:20][N:19]=[C:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:17]=1)([OH:3])=[O:1]

Participants

8

Reactant 4

HCID 962WaterHCID 3776IsopropanolHCID 6344DichloromethaneHCID 21710602HCID 21710602, compound

Product 1

HCID 21710592HCID 21710592, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 1118Sulfuric AcidSolventHCID 10219390chromium (VI) trioxideSolvent

Conditions

Temperature
21.5 °C

Procedure

2.5 g of 5-{2-[2-(1,3-dioxan-2-yl)ethyl]oxy-phenyl}-3-phenyl-1,2,4-oxadiazole are dissolved in 50 ml of acetone and at 0° C. a solution of chromium(VI)oxide in 30% sulphuric acid is added dropwise thereto. The mixture is then stirred for a further 20 hours at 20-23° C. and then 25 ml of isopropanol are added with cooling at 5° C. The mixture is added to a suspension of 100 ml of dichloromethane and 100 ml of water and the organic phase is separated off. The aqueous phase is extracted once more with dichloromethane and the combined organic solutions are again extracted with water. The extract is dried over sodium sulphate, evaporated down in vacuo and the residue is chromatographed on silica gel with dichloromethane/methanol (97:3). The product is recrystallised from ethyl acetate. Yield: 0.23 g (11% of theory), melting point 170-171° C.

Workup

  1. additionis added dropwise
  2. temperaturewith cooling at 5° C
  3. customthe organic phase is separated off
  4. extractionThe aqueous phase is extracted once more with dichloromethane
  5. extractionthe combined organic solutions are again extracted with water
  6. dry with materialThe extract is dried over sodium sulphate
  7. customevaporated down in vacuo
  8. customthe residue is chromatographed on silica gel with dichloromethane/methanol (97:3)
  9. customThe product is recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-8196062ae12d4942b8a6c706c5b58cc6
Source dataset
uspto-grants-2001_08
Patent number
US06277872B1

Reaction notes

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