Ethyl 2,2-dimethylhex-5-enoate → 2,2-Dimethylhex-5-en-1-ol

HRID 1511557

Reaktionsgleichung

Reaktionsgleichung von HRID 1511557
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][C:8]([CH3:18])([CH2:14][CH2:15][CH:16]=[CH2:17])[C:9](OCC)=[O:10]>CCOCC>[CH3:7][C:8]([CH3:18])([CH2:14][CH2:15][CH:16]=[CH2:17])[CH2:9][OH:10]

Komponenten

4

Edukt 2

HCID 14906730Ethyl 2,2-dimethylhex-5-enoateHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 102408212,2-Dimethylhex-5-en-1-olAusbeute 87,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Reaktionsbedingungen

Temperatur
22 °C

Versuchsvorschrift

To a stirred solution of 1M LAH in ether (142.14 mL, 142.14 mmol), at 0° C. and under nitrogen, was added dropwise ethyl 2,2-dimethylhex-5-enoate (11.00 g, 64.61 mmol) dissolved in 100 mL anhydrous ether over 1 hour. This reaction solution was stirred at 22° C. for 20 hours, then quenched with water (3 mL), 1M NaOH (11 mL) and water (9 mL), dried over Na2SO4, filtered and concentrated to give the title product (7.22 g, 87.09%). 1H NMR (500 MHz, CDCl3) δ 5.85-5.77 (m, 1H); 5.01 (d, 1H); 4.93 (d, 1H); 3.33 (d, 2H); 2.03 (m, 2H); 1.34 (m, 2H); 0.89 (m, 6H) ppm.

Aufarbeitung

  1. customquenched with water (3 mL), 1M NaOH (11 mL) and water (9 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-aa5c53fba5f14b629e9ca3488e75c42b
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08216999B2

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