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3-Methylbut-1-yne → N-(2-(3-Methylbut-1-ynyl)-5-nitrophenyl)butyramide

HRID 40118
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 40118
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][C:8]=1[NH:16][C:17](=[O:21])[CH2:18][CH2:19][CH3:20])(=O)=O.[CH3:24][CH:25]([CH3:28])[C:26]#[CH:27]>[N+](CCCC)(CCCC)(CCCC)CCCC.[I-].CC#N.CCN(CC)CC.[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:24][CH:25]([CH3:28])[C:26]#[C:27][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][C:8]=1[NH:16][C:17](=[O:21])[CH2:18][CH2:19][CH3:20]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 2

HCID 690193-Methylbut-1-yneHCID 112912342-Butyramido-4-nitrophenyl trifluoromethanesulfonate2×

Produkt 1

HCID 59762443N-(2-(3-Methylbut-1-ynyl)-5-nitrophenyl)butyramide

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 67553
Tetrabutylammonium Iodide
Katalysator
HCID 178418397HCID 178418397, VerbindungKatalysator
HCID 6342AcetonitrileLösungsmittel
HCID 8471TriethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A mixture of 2-butyramido-4-nitrophenyl trifluoromethanesulfonate (Compound 118, 200 mg, 0.56 mmol), CuI (32 mg, 0.17 mmol), and n-Bu4NI (311 mg, 0.84 mmol) in CH3CN (5 ml) and Et3N (1 ml) was purged with N2 for 10 min and Pd(PPh3)4 (64 mg, 0.056 mmol) was added and the mixture was purged with N2 for another 5 min. The mixture was then cooled to 0° C. and 3-methyl-1-butyne (76 mg, 1.12 mmol) was added. After 5 min, the reaction was quenched with aqueous NaHCO3, extracted with EtOAc (×3). The combined organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by chromatography on silica gel (0→20% EtOAc-hexanes) to yield the title compound.

Aufarbeitung

  1. customwas purged with N2 for 10 min
  2. customthe mixture was purged with N2 for another 5 min
  3. customthe reaction was quenched with aqueous NaHCO3
  4. extractionextracted with EtOAc (×3)
  5. washThe combined organic layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by chromatography on silica gel (0→20% EtOAc-hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-ff17125c20b24a54aa5ad4df529724f2
Quelldatensatz
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08524917B2

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