1-Octyne → HCID 13588520, Verbindung

HRID 1284439Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1284439
O1CC[CH2:4][CH2:3][CH:2]1[O:7][CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][O:9]1.[CH2:14](O)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]#[C:21][CH2:22]CCCCC.[CH:29]#CCCCCCC.C([Li])CCC.C(Br)CCCCCO>O1CCCC1.CCCCCC.CN(C)P(=O)(N(C)C)N(C)C.O>[C:8]([O:7][CH:2]([CH2:3][CH3:4])[CH3:29])(=[O:9])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:14]/[CH:15]=[CH:16]\[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Komponenten

10

Edukt 5

HCID 123701-OctyneHCID 779706-Bromo-1-hexanolHCID 263182Tetrahydropyranyl ether2×HCID 35630467-tetradecyn-1-olHCID 178418339Butyllithium

Produkt 1

HCID 13588520HCID 13588520, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8058HexaneLösungsmittelHCID 12679HexamethylphosphoramideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Tetrahydropyranyl ether derivative of 7-tetradecyne-1-ol. To a cooled solution (-15° C.) of 1-octyne (7.95 g) in 30 ml of dry tetrahydrofuran under a nitrogen atmosphere was added dropwise 30.4 ml of 2.09M butyllithium in hexane. The addition took 30 minutes, after which the reaction was warmed to 0° C. and then cooled to -10° C. This solution was added slowly to a cold (0° C.) solution of the tetrahydropyranyl ether derivative of hexamethylene bromohydrin (14.80 g) in 50 ml of hexamethylphosphoric triamide under nitrogen. The reaction mixture was allowed to warm to room temperature, stirred overnight, poured into cold water, and extracted three times with hexane. The combined organic layers were washed with water (three times) and brine, and dried with anhydrous Na2SO4. Removal of solvent under reduced pressure yielded 18.55 g of impure tetrahydropyranyl ether derivative of 7-tetradecyne-1-ol as a yellow oil. This material was used without further purification in the next step.

Aufarbeitung

  1. additionThe addition
  2. temperaturecooled to -10° C
  3. temperatureto warm to room temperature
  4. extractionextracted three times with hexane
  5. washThe combined organic layers were washed with water (three times) and brine
  6. dry with materialdried with anhydrous Na2SO4
  7. customRemoval of solvent under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-67481f5b33984f97a48a7964aecd40c6
Quelldatensatz
uspto-grants-1986_01
Patentnummer
US04563348

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