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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 594859Erstellt: 25. Oktober 2026

Sodium Carbonate → di-tert-butyl [6'-(3,6-dihydro-2H-pyran-4-yl)dispiro[1,3-oxazole-4,4'-chromene-3',3''-oxetan]-2-yl]imidodicarbonate

https://huagongshe.com/reaction/594859

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktSodium CarbonateHCID 10340—
Edukt3,6-Dihydro-2H-pyran-4-boronic acid pinacol esterHCID 11218053—
EduktDi-tert-butyl (6'-bromodispiro[1,3-oxazole-4,4'-chromene-3',3''-oxetan]-2-yl)imidodicarbonateHCID 86724239—
KatalysatorHCID 178418476HCID 178418476—
LösungsmittelWaterHCID 962—
Lösungsmittel1,4-DioxaneHCID 31275—
Produktdi-tert-butyl [6'-(3,6-dihydro-2H-pyran-4-yl)dispiro[1,3-oxazole-4,4'-chromene-3',3''-oxetan]-2-yl]imidodicarbonateHCID 86724255—

Reaktionsbedingungen

Temperatur100 °C

Reaktionsschritte

A mixture of di-tert-butyl (6′-bromodispiro[1,3-oxazole-4,4′-chromene-3′,3″-oxetan]-2-yl)imidodicarbonate (300 mg, 0.571 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-2H-pyran (360 mg, 1.71 mmol), bis(triphenylphosphine)palladium(II) dichloride (40.1 mg, 0.057 mmol) and Na2CO3 (182 mg, 1.71 mmol) in dioxane (3.6 mL) and water (0.9 mL) was stirred for 1 hour at 100° C. The mixture was cooled down to ambient temperature and partitioned between EtOAc and water. The organic layer was washed with brine, dried over MgSO4, diluted with hexane, and filtered through silica gel pad (eluted with 50% EtOAc in hexane). The filtrate was concentrated at reduced pressure to give crude di-tert-butyl[6′-(3,6-dihydro-2H-pyran-4-yl)dispiro[1,3-oxazole-4,4′-chromene-3′,3″-oxetan]-2-yl]imidodicarbonate which was used for the next reaction without further purification.

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS09242973B2
Quelldatensatzuspto-grants-2016_01
ORD IDord-294ec41c494248e4b80280aa176b52fb
Quellennotizuspto-grants-2016_01