Tetrahydrofuran → 2-Tridecen-1-ol

HRID 2396552

반응식

HRID 2396552 반응식
[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]

참가 물질

8

반응물 3

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

생성물 2

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

시약·촉매·용매 3

HCID 167780Copper(II) nitrate hemipentahydrate촉매HCID 11459718Rhodium chloride trihydrate촉매HCID 962Water용매

실험 절차

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.

출처 및 근거

ORD 기록
ord-6900572539fe4576aba8b20a7d049227
출처 데이터셋
uspto-grants-1996_02
특허 번호
US05492964

연결된 노트

불러오는 중…