Lithium hydride → (1RS,4SR,5RS)-4-(4,8-dimethyl-5-oxo-7-nonenyl)-4-methyl-3,8-dioxabicyclo[3.2.1]octane-1-ethanol

HRID 2058140Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2058140
[C:1]([CH:4]([CH3:20])[CH2:5][CH2:6][CH2:7][C:8]1([CH3:19])[CH:14]2[O:15][C:11]([CH2:16][CH2:17][OH:18])([CH2:12][CH2:13]2)[CH2:10][O:9]1)([OH:3])=O.[H-].[Li+].[CH3:23][C:24]([CH3:28])=[CH:25][CH2:26][Li].C(=O)(O)[O-].[Na+]>CCOCC>[CH3:20][CH:4]([C:1](=[O:3])[CH2:26][CH:25]=[C:24]([CH3:28])[CH3:23])[CH2:5][CH2:6][CH2:7][C:8]1([CH3:19])[CH:14]2[O:15][C:11]([CH2:16][CH2:17][OH:18])([CH2:12][CH2:13]2)[CH2:10][O:9]1

Komponenten

6

Edukt 4

HCID 62714Lithium hydrideHCID 516892Sodium BicarbonateHCID 23349564(1RS,4SR,5RS)-4-(4-carboxypentyl)-4-methyl-3,8-dioxabicyclo[3.2.1]octane-1-ethanolHCID 178506861C5H9Li

Produkt 1

HCID 13367193(1RS,4SR,5RS)-4-(4,8-dimethyl-5-oxo-7-nonenyl)-4-methyl-3,8-dioxabicyclo[3.2.1]octane-1-ethanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

A mixture of (1RS,4SR,5RS)-4-(4-carboxypentyl)-4-methyl-3,8-dioxabicyclo[3.2.1]octane-1-ethanol (58 mg, 0.2 mM), lithium hydride (10 mg, 1.25 mM) and ether (5 ml) is stirred at room temperature under nitrogen for two hours. An excess of 3-methyl-2-butenyl lithium is added to this mixture at room temperature. The resulting mixture is stirred for two hours and then treated with 5% sodium bicarbonate solution (5 ml) and extracted with ethyl acetate (3×20 ml). The combined organic layers are dried (Na2SO4), evaporated in vacuo and the residue is purified by column chromatography on silica gel (7 g) with ether to give (1RS,4SR,5RS)-4-(4,8-dimethyl-5-oxo-7-nonenyl)-4-methyl-3,8-dioxabicyclo[3.2.1]octane-1-ethanol (13 mg), 25%) as a colorless oil).

Aufarbeitung

  1. stirringThe resulting mixture is stirred for two hours
  2. extractionextracted with ethyl acetate (3×20 ml)
  3. dry with materialThe combined organic layers are dried (Na2SO4)
  4. customevaporated in vacuo
  5. customthe residue is purified by column chromatography on silica gel (7 g) with ether

Quellen und Nachweise

ORD-Eintrag
ord-a8ae85c058c04db295b282d2515d123f
Quelldatensatz
uspto-grants-1980_07
Patentnummer
US04215048

Notizen zur Reaktion

Wird geladen…