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

HRID 617069Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 617069
[OH:1][CH:2]1[CH2:6][C:5](=[O:7])[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:3]1.[O:19]1[CH:24]=[CH:23][CH2:22][CH2:21][CH2:20]1.[Cl-].[Na+].C(=O)(O)[O-].[Na+]>CCOCC.CO.C(Cl)Cl>[O:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH:20]1[O:1][CH:2]1[CH2:6][C:5](=[O:7])[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:3]1

Komponenten

8

Edukt 4

HCID 5234Sodium ChlorideHCID 80803,4-dihydro-2H-pyranHCID 516892Sodium BicarbonateHCID 98379417-(3-Hydroxy-5-oxo-1-cyclopentenyl)-heptanoic acid ethyl ester

Produkt 1

HCID 131895154-Tetrahydropyranyloxy-2-(6-carbethoxyhexyl)cyclopent-2-en-1-one

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of 674 mg. (2.64 mmoles) of 4-hydroxy-2-(6-carbethoxyhexyl)cyclopent-2-en-1-one (Example 29) and 2.22 g. (26.4 mmoles) of dihydropyran in 2.6 ml. of methylene chloride is added 5.0 mg. (0.026 mmoles) of p-toluenesulonic acid monohydrate. After stirring for 20 minutes at room temperature the solution is diluted with ether and poured into saturated sodium chloride solution containing a little sodium bicarbonate. The organic phase is separated and washed with saturated sodium chloride solution. The extract is dried over magnesium sulfate, and volatile matter is evaporated at reduced pressure to give an oil, λmax.MeOH = 224 mμ (7950); θmax. = 1735 (ester carbonyl group), 1710 (ketone carbonyl group), and 1030 cm-1 (tetrahydropyranyloxy group).

Aufarbeitung

  1. customThe organic phase is separated
  2. washwashed with saturated sodium chloride solution
  3. dry with materialThe extract is dried over magnesium sulfate, and volatile matter
  4. customis evaporated at reduced pressure
  5. customto give an oil, λmax

Quellen und Nachweise

ORD-Eintrag
ord-a42c5ad4a447486dac9a1c0d7e30e9d5
Quelldatensatz
uspto-grants-1978_02
Patentnummer
US04076947

Notizen zur Reaktion

Wird geladen…