Tetrahydrofuran → 2-Tridecen-1-ol

HRID 2396552

Reaction equation

HRID 2396552 reaction equation
[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]

Participants

8

Reactant 3

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

Product 2

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

Reagents, catalysts & solvents 3

HCID 167780Copper(II) nitrate hemipentahydrateCatalystHCID 11459718Rhodium chloride trihydrateCatalystHCID 962WaterSolvent

Procedure

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.

Sources & evidence

ORD record
ord-6900572539fe4576aba8b20a7d049227
Source dataset
uspto-grants-1996_02
Patent number
US05492964

Linked notes

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