Tetrahydrofuran → 2-Tridecen-1-ol

HRID 2396552

反応式

HRID 2396552 の反応式
[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]

参加物

8

反応物 3

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

生成物 2

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

試薬・触媒・溶媒 3

HCID 167780Copper(II) nitrate hemipentahydrate触媒HCID 11459718Rhodium chloride trihydrate触媒HCID 962Water溶媒

実験手順

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.

出典と根拠

ORDレコード
ord-6900572539fe4576aba8b20a7d049227
出典データセット
uspto-grants-1996_02
特許番号
US05492964

関連ノート

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