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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 1501945Erstellt: 26. Oktober 2026

Triethylamine → (3R)-6-ethenyl-3-methyl-3,4-dihydro-1H-isochromen-1-one

https://huagongshe.com/reaction/1501945

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktTriethylamineHCID 8471—
EduktPotassium vinyltrifluoroborateHCID 23679353—
Edukt(3R)-6-bromo-3-methyl-3,4-dihydro-1H-isochromen-1-oneHCID 71270763—
KatalysatorHCID 178418807HCID 178418807—
LösungsmittelEthanolHCID 702—
LösungsmittelChloroformHCID 6212—
Produkt(3R)-6-ethenyl-3-methyl-3,4-dihydro-1H-isochromen-1-oneHCID 86727028—

Reaktionsbedingungen

Temperatur100 °C

Reaktionsschritte

A solution of (3R)-6-bromo-3-methyl-3,4-dihydro-1H-isochromen-1-one (2.4 g, 9.96 mmol) and triethylamine (2.78 mL, 19.91 mmol) in EtOH (39.8 mL) was added to a microwave vial containing PdCl2(dppf)-CH2Cl2, (0.406 g, 0.498 mmol) and potassium vinyltrifluoroborate (2.000 g, 14.93 mmol). The contents of the vial were heated to 100° C. for 1 hour after which the mixture was cooled, diluted with chloroform (50 mL) and washed with aqueous ammonium chloride (25 mL). The organic layer was then dried over magnesium sulfate, filtered and the solvent was evaporated under reduced pressure. MPLC purification (15-60% EtOAc/Hex) gave the title compound.

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS09206199B2
Quelldatensatzuspto-grants-2015_12
ORD IDord-75f27879dd2c4c20a5a8b4bb2c8a7392
Quellennotizuspto-grants-2015_12