HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium hydride → 5-(3-bromo-2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 2-Chloromethyl 2-(trimethylsilyl)ethyl ether | HCID 2724271 | — |
| Reactant | 4-(3-bromo-2-methoxyphenyl)-1H-imidazole | HCID 22018593 | — |
| Product | 5-(3-bromo-2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole | HCID 22018655 | 60% |
Reaction Steps
Reaction of 5-(3-bromo-2-methoxy-phenyl)-1H-imidazole (539 mg, 3.10 mmol), NaH (60%, 120 mg, 3.00 mmol), and SEMCl (751 uL, 3.61 mmol) followed by column chromatography on silica gel (hexane/EtOAC 3:2) gave the title compound (485 mg, 60%) as a brown oil. 1H NMR (300 MHz, CDCl3) δ0.00 (s, 9H), 0.93 (t, 2H, J=7.5 Hz), 3.52 (t, 2H, J=7.5 Hz), 3.93 (s, 3H), 5.31 (s, 2H), 6.82 (d, 1H, J=6.0 Hz), 7.31 (dd, 1H, J=9.0, 3.0 Hz), 7.63 (s, 1H), 7.66 (s, 1H), 8.36 (d, 1H, J=2.1 Hz). ES-MS m/z 385 (M+H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06864265B2 |
| Source dataset | uspto-grants-2005_03 |
| ORD ID | ord-00523f6a67bd40ebbdc3848112ae352b |
| Source note | uspto-grants-2005_03 |