Ammonium Chloride → 3,7,11-Trimethyl-12-(2-tetrahydropyranyl)oxy-1,6,10-dodecatrien-3-ol

HRID 5661

Reaktionsgleichung

Reaktionsgleichung von HRID 5661
[CH3:1][C:2]([CH2:9][CH2:10][CH:11]=[C:12]([CH3:21])[CH2:13][O:14][CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][O:16]1)=[CH:3][CH2:4][CH2:5][C:6](=[O:8])[CH3:7].[CH:22]([Mg]Br)=[CH2:23].[Cl-].[NH4+]>O1CCCC1>[CH3:7][C:6]([OH:8])([CH2:5][CH2:4][CH:3]=[C:2]([CH3:1])[CH2:9][CH2:10][CH:11]=[C:12]([CH3:21])[CH2:13][O:14][CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][O:16]1)[CH:22]=[CH2:23]

Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 539858946,10-Dimethyl-11-(2-tetrahydropyranyl)oxy-5,9-undecadien-2-oneHCID 178418507HCID 178418507, Verbindung

Produkt 1

HCID 678485313,7,11-Trimethyl-12-(2-tetrahydropyranyl)oxy-1,6,10-dodecatrien-3-olAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of 6,10-dimethyl-11-(2-tetrahydropyranyl) oxy-5,9-undecadien-2-one (80 mg, 0.27 mmol) in tetrahydrofuran (3 ml) was stirred on an ice bath under argon atmosphere. To the solution was added vinylmagnesium bromide in tetrahydrofuran (0.3 ml, 0.3 mmol, 1.0 M), and the mixture was warmed to room temperature and stirred for 10 hours. After addition of saturated aqueous ammonium chloride (2 ml), the reaction mixture was extracted with ether. The extract was dried over Na2SO4 and evaporated in vacuo to remove the solvent to give a crude product, which was purified with silica gel column chromatography to obtain 3,7,11-trimethyl-12-(2-tetrahydropyranyl)oxy-1,6,10-dodecatrien-3-ol (61 mg, 70%). IR(film)cm-1 ; 3460, 2950, 2880, 1200, 1118, 1075, 1022, 905, 865, 810.

Aufarbeitung

  1. extractionthe reaction mixture was extracted with ether
  2. dry with materialThe extract was dried over Na2SO4
  3. customevaporated in vacuo
  4. customto remove the solvent
  5. customto give a crude product, which
  6. customwas purified with silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-040d953b7c4342fe86b15659471a5179
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05245085

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