1-Chlorohexadecane → 1-[(tetrahydro-2H-pyran-2-yl)oxy]eicosan-4-ol

HRID 1086683

Reaktionsgleichung

Reaktionsgleichung von HRID 1086683
[Mg].Cl[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].C[Mg]Br.[O:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH:23]1[O:28][CH2:29][CH2:30][CH2:31][CH:32]=[O:33]>C(OCC)C.C(Br)C>[O:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH:23]1[O:28][CH2:29][CH2:30][CH2:31][CH:32]([OH:33])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH3:3]

Komponenten

7

Edukt 4

HCID 209931-ChlorohexadecaneHCID 551206Butanal, 4-[(tetrahydro-2H-pyran-2-yl)oxy]-HCID 5462224MagnesiumHCID 178418573HCID 178418573, Verbindung

Produkt 1

HCID 157356851-[(tetrahydro-2H-pyran-2-yl)oxy]eicosan-4-olAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittel3×HCID 6332Ethyl BromideLösungsmittel

Versuchsvorschrift

To a refluxing mixture of 1.26 g of magnesium turnings, 15.5 ml of 1-chlorohexadecane, and 100 ml of anhydrous diethyl ether were added 0.5 ml of a 3.2M solution of methylmagnesium bromide in diethyl ether and 0.05 ml of ethyl bromide. The reaction mixture was refluxed for a period of 6 hours. A solution of 3.0 g of 4-[(tetrahydro-2H-pyran-2-yl)oxy]butanal in 10 ml of diethyl ether was added, and the reaction mixture refluxed for an additional hour. The reaction mixture was poured into a mixture of ice and a saturated aqueous solution of ammonium chloride, and filtered. Upon standing the filtrate separated into organic and inorganic phases. The organic phase was dried over anhydrous sodium sulfate and concentrated to an oil. Flash chromatography of the oil utilizing 25% diethyl ether/petroleum ether yielded 4.8 g (70%) of 1-[(tetrahydro-2H-pyran-2-yl)oxy]eicosan-4-ol as a solid, mp 39°-43°.

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed for a period of 6 hours
  2. temperaturethe reaction mixture refluxed for an additional hour
  3. additionThe reaction mixture was poured into a mixture of ice
  4. filtrationa saturated aqueous solution of ammonium chloride, and filtered
  5. customseparated into organic and inorganic phases
  6. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  7. concentrationconcentrated to an oil

Quellen und Nachweise

ORD-Eintrag
ord-23460b9557cf4b6bbd2f36088e231a8f
Quelldatensatz
uspto-grants-1991_07
Patentnummer
US05030733

Verknüpfte Notizen

Wird geladen…