Tetrahydrofuran → 2-Tridecen-1-ol

HRID 2396552

Reaktionsgleichung

Reaktionsgleichung von HRID 2396552
[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].C(O[SiH](OCC)OCC)C.C1COCC1>O.O.O.[Rh](Cl)(Cl)Cl.O.[N+]([O-])([O-])=O.[Cu+2].O.O.O.O.[N+]([O-])([O-])=O.[Cu+2].[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.O>[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].[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

8

Edukt 3

HCID 8028TetrahydrofuranHCID 13830TriethoxysilaneHCID 111169792-Tridecyn-1-ol

Produkt 2

HCID 1103702-Tridecen-1-olAusbeute 192 %HCID 5364998(Z)-2-Tridecen-1-ol

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167780Copper(II) nitrate hemipentahydrateKatalysatorHCID 11459718Rhodium chloride trihydrateKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

Z-2-Tridecen-1-ol was prepared according to the method of Example 6 using 2-tridecyn-1-ol (98 mg, 0.5 mmol), rhodium(III) chloride trihydrate (1.3 mg, 0.005 mmol), copper(II) nitrate hemipentahydrate (5.8 mg, 0.025 mmol), triethoxysilane (0.21 g, 0.23 mL, 1.25 mmol), THF (2.5 mL) and water (0.5 mL) at room temperature for 8 hours to afford 96 mg (0.48 mmol, 97%) of 2-tridecene-1-ol which was a 6:1 Z:E mixture by spectroscopic analysis. Spectral analysis of the Z-isomer: IR (neat) 3337.2, 2924.8, 2854.6, 1462.6, 1016.2 cm-1 : 1H NMR (300 MHz, CDCl3) δ 5.56 (m, 2 H), 4.17 (d, J=5.9 Hz, 2H), 2.04 (br p, 2 H), 1.24 (m, 17 H), 0.86 (t, J=6.7 Hz, 3H); 13C NMR (75 MHz, CDCl3) δ 1133.22, 58.58, 31.91, 29.62, 29.49, 29.34, 29.23, 27.44, 22.69, 15.24, 14.11.

Quellen und Nachweise

ORD-Eintrag
ord-6900572539fe4576aba8b20a7d049227
Quelldatensatz
uspto-grants-1996_02
Patentnummer
US05492964

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