Sodium hydride → 5-tert-butyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole

반응식

[C:1]([C:5]1[NH:9][CH:8]=[N:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:12][Si:13]([CH2:16][CH2:17][O:18][CH2:19]Cl)([CH3:15])[CH3:14]>>[C:1]([C:5]1[N:9]([CH2:19][O:18][CH2:17][CH2:16][Si:13]([CH3:15])([CH3:14])[CH3:12])[CH:8]=[N:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

참가 물질

반응물 3

HCID 24758Sodium hydride

HCID 4984365-tert-butyl-1H-imidazole

HCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl ether

생성물 1

HCID 220185695-tert-butyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole수율 57.6%

실험 절차

Reaction of 5-tert-butyl-1H-imidazole (423 mg, 3.41 mmol), NaH (60%, 132 mg, 3.31 mmol), and SEMCl (639 uL, 3.61 mmol) followed by column chromatography on silica gel (hexane/EtOAC 3:2) gave the title compound (500 mg, 57%) as a yellow oil. 1H NMR (300 MHz, CDCl3) δ major isomer: 0.00 (s, 9H), 0.89 (t, 2H, J=7.5 Hz), 1.29 (s, 9H), 3.47 (t, 2H, J=7.5 Hz), 5.19 (s, 2H), 6.73 (s, 1H), 7.50 (s, 1).

출처 및 근거

ORD 기록: ord-0a0e3ab9f473443fad7ae8fa40b424dd
출처 데이터셋: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US06864265B2

반응 노트

불러오는 중…