Methyl iodide → HCID 12723453, Verbindung

HRID 1583187Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1583187
[H-].[Na+].[CH:3]1([OH:10])[CH2:8][CH2:7]C(O)C=C1.[CH3:11]I.[CH2:13]1[CH2:17][O:16][CH2:15][CH2:14]1>>[CH3:15][O:16][CH:17]1[CH2:13][CH2:14][CH:3]([O:10][CH3:11])[CH:8]=[CH:7]1

Komponenten

5

Edukt 4

HCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 5508252-Cyclohexene-1,4-diol

Produkt 1

HCID 12723453HCID 12723453, VerbindungAusbeute 91 %

Versuchsvorschrift

Lit., J. Org. Chem., 53:5695 (1988). To 14.3 g (328 mmol) sodium hydride (55% dispersion in oil) was added dropwise at 0° C. with stirring a solution of 10.1 g (88.5 mmol) (1RS,4RS)-cyclohex-2-ene-1,4-diol in 100 ml THF. 34 ml (546 mmol) methyl iodide was then added and stirring continued for an additional 48 h at room temperature. The reaction was quenched with saturated ammonium chloride solution and extracted with ether. The combined organic extracts were washed successively with saturated ammonium chloride solution and saturated brine, dried over sodium sulphate, and concentrated in vacuo to afford 11.5 g (91%) of the title compound as a yellow oil. 1H NMR d (250 MHz, CDCl3) 5.90 (2H, s), 3.82 (2H, br t), 3.37 (6H, s), 2.10 (2H, m), 1.51 (2H, m).

Aufarbeitung

  1. customThe reaction was quenched with saturated ammonium chloride solution
  2. extractionextracted with ether
  3. washThe combined organic extracts were washed successively with saturated ammonium chloride solution and saturated brine
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-292fdc128ced4a139e8daac78800770f
Quelldatensatz
uspto-grants-2004_05
Patentnummer
US06740760B2

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