Reaction #7203

ord-80ab18e9c9bf4fefb0d2677227570bf5

Reaction equation

CC(C)(C)c1cnc[nH]1
5-tert-butyl-1H-imidazole
[H-].[Na+]
NaH
C[Si](C)(C)CCOCCl
SEMCl
→
CC(C)(C)c1cncn1COCC[Si](C)(C)C
title compound
Yield 57.6%
CC(C)(C)c1cncn1COCC[Si](C)(C)C
5-tert-Butyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole
Yield 57.6%

Reactants

CC(C)(C)c1cnc[nH]1
5-tert-butyl-1H-imidazole
[H-].[Na+]
NaH
C[Si](C)(C)CCOCCl
SEMCl

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

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, 1H).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07084155B2uspto-grants-2006_08