HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → [4-(3,3-Dimethyl-but-1-ynyl)-phenyl]-carbamic acid tert-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 3,3-Dimethyl-1-butyne | HCID 13512 | — |
| Reactant | tert-butyl N-(4-iodophenyl)carbamate | HCID 2773612 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | Dichlorobis(triphenylphosphine)palladium | HCID 6102075 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | [4-(3,3-Dimethyl-but-1-ynyl)-phenyl]-carbamic acid tert-butyl ester | HCID 54041145 | — |
Reaction Steps
(4-Iodo-phenyl)-carbamic acid tert-butyl ester (37a, 1.0 g, 3.13 g) was dissolved in THF (30 mL) and treated with Et3N (2.2 mL, 15.7 mmol), 3,3-dimethyl- 1-butyne (0.58 mL, 4.70 mmol), bis(triphenylphosphine) palladium (II) chloride (0.218 g, 0.31 mmol), and copper (I) iodide (0.03 g, 0.16 mmol). The reaction was stirred overnight at room temperature, then filtered and concentrated. The residue was chromatographed on silica gel eluting with 8:1 hexanes/EtOAc to give 0.7 g (82%) of the mostly clean desired product which was carried on without further purification.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06251919B1 |
| Source dataset | uspto-grants-2001_06 |
| ORD ID | ord-b7f7edb3e6ca4fadb3e54c6928262d62 |
| Source note | uspto-grants-2001_06 |