HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → Tert-butyl 2-methoxy-6-((trimethylsilyl)ethynyl)phenylcarbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Trimethylsilylacetylene | HCID 66111 | — |
| Reactant | Tert-butyl 2-iodo-6-methoxyphenylcarbamate | HCID 10760198 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | Tert-butyl 2-methoxy-6-((trimethylsilyl)ethynyl)phenylcarbamate | HCID 10829462 | 98% |
Reaction Steps
To tert-butyl 2-iodo-6-methoxyphenylcarbamate (10.36 g, 29.67 mmol), ethynyltrimethylsilane (3.20 g, 32.63 mmol), copper(I) iodide (0.28 g, 1.48 mmol), and PdCl2(PPh3)2 (1.04 g, 1.48 mmol) in THF (100 mL) was added triethylamine (3.60 g, 35.6 mmol), followed by overnight stirring. The crude reaction was then concentrated and the mixture was flashed through silica gel with 10:1 Hex/EtOAc to give the desired product (98%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08138181B2 |
| Source dataset | uspto-grants-2012_03 |
| ORD ID | ord-07447271bdc54d76b1831bd524957de7 |
| Source note | uspto-grants-2012_03 |