3-Methoxypropyne → Di-tert-butyl [6'-(3-methoxyprop-1-yn-1-yl)dispiro[1,3-oxazole-4,4'-chromene-3',3''-oxetan]-2-yl]imidodicarbonate

HRID 594857

Reaktionsgleichung

Reaktionsgleichung von HRID 594857
Br[C:2]1[CH:3]=[C:4]2[C:31](=[CH:32][CH:33]=1)[O:30][CH2:29][C:25]1([CH2:28][O:27][CH2:26]1)[C:5]12[CH2:9][O:8][C:7]([N:10]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[N:6]1.[CH3:34][O:35][CH2:36][C:37]#[CH:38]>CCN(CC)CC.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>[C:14]([O:13][C:11]([N:10]([C:7]1[O:8][CH2:9][C:5]2([N:6]=1)[C:25]1([CH2:26][O:27][CH2:28]1)[CH2:29][O:30][C:31]1[C:4]2=[CH:3][C:2]([C:38]#[C:37][CH2:36][O:35][CH3:34])=[CH:33][CH:32]=1)[C:18]([O:20][C:21]([CH3:23])([CH3:24])[CH3:22])=[O:19])=[O:12])([CH3:15])([CH3:16])[CH3:17]

Komponenten

5

Edukt 2

HCID 693933-MethoxypropyneHCID 86724239Di-tert-butyl (6'-bromodispiro[1,3-oxazole-4,4'-chromene-3',3''-oxetan]-2-yl)imidodicarbonate

Produkt 1

HCID 86724253Di-tert-butyl [6'-(3-methoxyprop-1-yn-1-yl)dispiro[1,3-oxazole-4,4'-chromene-3',3''-oxetan]-2-yl]imidodicarbonateAusbeute 23,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

A mixture of di-tert-butyl (6′-bromodispiro[1,3-oxazole-4,4′-chromene-3′,3″-oxetan]-2-yl)imidodicarbonate (150 mg, 0.286 mmol) and 3-methoxyprop-1-yne (0.072 mL, 0.86 mmol) in Et3N (1.5 mL) was purged with argon. To the mixture was added Pd(PPh3)4 (13 mg, 0.011 mmol) and CuBr (4.9 mg, 0.034 mmol), and the mixture was refluxed for 3 hours under an argon atmosphere. The mixture was partitioned between CHCl3 and brine, and filtered through celite. The organic layer of the filtrate was dried over MgSO4, filtered off, and the filtrate was evaporated. Silicagel column chromatography (EtOAc-hexane, a linear gradient of EtOAc from 0 to 25%) afforded di-tert-butyl[6′-(3-methoxyprop-1-yn-1-yl)dispiro[1,3-oxazole-4,4′-chromene-3′,3″-oxetan]-2-yl]imidodicarbonate (34.7 mg).

Aufarbeitung

  1. customwas purged with argon
  2. temperaturethe mixture was refluxed for 3 hours under an argon atmosphere
  3. customThe mixture was partitioned between CHCl3 and brine
  4. filtrationfiltered through celite
  5. dry with materialThe organic layer of the filtrate was dried over MgSO4
  6. filtrationfiltered off
  7. customthe filtrate was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-ff0f91a0a1934f7ea4b6b60477827d24
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242973B2

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