Potassium sodium tartarate → 2-Tridecen-1-ol, (2E)-

HRID 2255029

Reaktionsgleichung

Reaktionsgleichung von HRID 2255029
[CH2:1]([OH:14])[C:2]#[C:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].[H-].[H-].[H-].[H-].[Li+].[Al+3].C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>CCOCC>[CH2:1]([OH:14])/[CH:2]=[CH:3]/[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Komponenten

5

Edukt 3

HCID 9855836Potassium sodium tartarateHCID 111169792-Tridecyn-1-olHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 53649492-Tridecen-1-ol, (2E)-

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a solution of 2-tridecyn-1-ol (2 g, 10 mmol) in Et2O (50 mL) was added LiAlH4 (1 g, 26 mmol, 2.6 equiv). The resulting mixture was refluxed for 12 hours and allowed to cool to 25° C. A saturated solution of sodium-potassium tartrate was then added and the resulting mixture was stirred for an additional 3 hours. The organic layer was separated, dried (MgSO2) and concentrated by rotary evaporation to yield trans-2-tridecen-1-ol (50) as a colorless oil: 1H NMR (CDCl3) δ 5.62 (dt, J1 =15.3 Hz, J2 =5.1 Hz, 1 H), 5.70 (dt, J1 =15.3 Hz, J2 =5.7 Hz, 1 H), 4.08 (t, J=4.2 Hz, 2 H), 2.04 (q, J=6 Hz, 2 H), 1 30 (m, 16 H), 0.88 (t, J=6.9 Hz, 3 H); 13C NMR (CDCl3) δ 133.72, 128.92, 63.96, 32.31, 32.01, 29.72, 29.60, 29.43, 29.28, 29.24, 22.78, 14.20. ##STR24##

Aufarbeitung

  1. temperatureThe resulting mixture was refluxed for 12 hours
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO2)
  4. concentrationconcentrated by rotary evaporation

Quellen und Nachweise

ORD-Eintrag
ord-3c5521d99e2b4f55b2e2a69221772d49
Quelldatensatz
uspto-grants-1993_08
Patentnummer
US05238832

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