Triethylamine → [4-(3,3-Dimethyl-but-1-ynyl)-phenyl]-carbamic acid tert-butyl ester

HRID 1069184Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1069184
[C:1]([O:5][C:6](=[O:15])[NH:7][C:8]1[CH:13]=[CH:12][C:11](I)=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.[CH3:23][C:24]([CH3:28])([CH3:27])[C:25]#[CH:26]>C1COCC1.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cu]I>[C:1]([O:5][C:6](=[O:15])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:26]#[C:25][C:24]([CH3:28])([CH3:27])[CH3:23])=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

7

Edukt 3

HCID 8471TriethylamineHCID 135123,3-Dimethyl-1-butyneHCID 2773612tert-butyl N-(4-iodophenyl)carbamate

Produkt 1

HCID 54041145[4-(3,3-Dimethyl-but-1-ynyl)-phenyl]-carbamic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 6102075Dichlorobis(triphenylphosphine)palladiumKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

(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.

Aufarbeitung

  1. filtrationfiltered
  2. concentrationconcentrated
  3. customThe residue was chromatographed on silica gel eluting with 8:1 hexanes/EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-b7f7edb3e6ca4fadb3e54c6928262d62
Quelldatensatz
uspto-grants-2001_06
Patentnummer
US06251919B1

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