Sodium Chloride → 4-Tetrahydropyranyloxy-2-(6-tetrahydropyranylcarboxyhexyl)cyclopent-2-en-1-one

HRID 261913

Reaktionsgleichung

Reaktionsgleichung von HRID 261913
[C:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[C:11](=[O:16])[CH2:12][CH:13]([OH:15])[CH:14]=1)([OH:3])=[O:2].[O:17]1[CH:22]=[CH:21][CH2:20][CH2:19][CH2:18]1.O.[C:24]1(C)C=[CH:28][C:27](S(O)(=O)=O)=[CH:26][CH:25]=1.C(=O)(O)[O-:36].[Na+].[Cl-].[Na+]>CO.O.CCOCC.C(Cl)Cl>[O:17]1[CH2:18][CH2:19][CH2:20][CH2:21][CH:22]1[O:15][CH:13]1[CH2:12][C:11](=[O:16])[C:10]([CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH:4]([C:1]([OH:3])=[O:2])[CH:28]2[CH2:27][CH2:26][CH2:25][CH2:24][O:36]2)=[CH:14]1

Komponenten

10

Edukt 5

HCID 5234Sodium ChlorideHCID 80803,4-dihydro-2H-pyranHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 3690897ACMC-20apjz

Produkt 1

HCID 704200994-Tetrahydropyranyloxy-2-(6-tetrahydropyranylcarboxyhexyl)cyclopent-2-en-1-one

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of 5.59 g. (24.6 mmoles) of 4-hydroxy-2-(6-carboxyhexyl)cyclopent-2-en-1-one (Example 28) and 20.7 g. (246 mmoles) of dihydropyran in 100 ml. of methylene chloride at 20° C. is added 47 mg. (0.246 mmoles) of p-toluenesulfonic acid monohydrate in one portion. The temperature is maintained at 20°-25° C. by cooling and is stirred for one hour at that temperature. The solution is diluted with 200 ml. of ether and poured into a mixture of 40 ml. of saturated sodium bicarbonate solution, 40 ml. of saturated sodium chloride solution, and 80 ml. of water. The phases are separated and the aqueous phase is extracted with additional ether. The total extract is washed successively with water and saturated sodium chloride solution, dried over potassium carbonate, and freed of volatile matter by concentration at reduced pressure to give an oil, λmax.MeOH =223 mμ (9500); νmax. 1730 (ester carbonyl group), 1705 (ketone carbonyl group), and 1030-1 (tetrahydropyranyloxy groups).

Aufarbeitung

  1. temperatureThe temperature is maintained at 20°-25° C.
  2. temperatureby cooling
  3. additionThe solution is diluted with 200 ml
  4. customThe phases are separated
  5. extractionthe aqueous phase is extracted with additional ether
  6. extractionThe total extract
  7. washis washed successively with water and saturated sodium chloride solution
  8. dry with materialdried over potassium carbonate
  9. concentrationfreed of volatile matter by concentration at reduced pressure
  10. customto give an oil, λmax

Quellen und Nachweise

ORD-Eintrag
ord-23839d36a98e438ba480b450f8b4e1cc
Quelldatensatz
uspto-grants-1979_05
Patentnummer
US04152524

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