Cycloheptanone → 2-[(Tetrahydropyranyloxy)acetyl]cycloheptanone

HRID 1034350

Reaktionsgleichung

Reaktionsgleichung von HRID 1034350
[C:1]1(=[O:8])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[O:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]1[O:15][CH2:16][C:17](OCC)=[O:18].[H-].[Na+].[NH4+].[Cl-]>CCOCC.CCO.CO.CCCCCC>[O:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]1[O:15][CH2:16][C:17]([CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:1]1=[O:8])=[O:18]

Komponenten

9

Edukt 4

HCID 10400CycloheptanoneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 10899396ethyl 2-((tetrahydro-2H-pyran-2-yl)oxy)acetate

Produkt 1

HCID 149651552-[(Tetrahydropyranyloxy)acetyl]cycloheptanoneAusbeute 88,2 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 702EthanolKatalysatorHCID 887MethanolLösungsmittelHCID 3283Diethyl EtherLösungsmittel2×HCID 8058HexaneLösungsmittel

Versuchsvorschrift

A solution of 2.80 g (25 mmol) of cycloheptanone and 4.71 g (25 mmol) of ethyl (tetrahydropyranyloxy)acetate (Ireland, R. E.; Wipf, P. Tetrahedron Lett., 1989, 30, 919-22) in 20 mL of Et2O was added over the course of 1 h to an ice-cold, stirring mixture of hexane-washed NaH and 0.12 mL (2 mmol, 0.092 g) of absolute EtOH in 10 mL of Et2O under N2. The light brown mixture was allowed to warm to room temperature and was stirred overnight. MeOH (5 mL) was added and the solution was poured onto 200 mL of saturated aqueous NH4Cl. After acidification to pH 2 with 1N aqueous HCl, the mixture was extracted with Et2O. The organic layer was washed with brine, dried over Na2SO4, and concentrated to give 5.61 g of crude 2-[(tetrahydropyranyloxy)acetyl]cycloheptanone as a light brown oil.

Aufarbeitung

  1. stirringwas stirred overnight
  2. extractionAfter acidification to pH 2 with 1N aqueous HCl, the mixture was extracted with Et2O
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-0fc612491b464df2ad9d3ebe63f66487
Quelldatensatz
uspto-grants-1994_05
Patentnummer
US05315012

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