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

HRID 2281308Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[O:7][C@H:6]([CH3:13])[CH2:5]2.[CH2:14](N(CC)CC)[CH3:15].C([B-](F)(F)F)=C.[K+]>CCO.C(Cl)(Cl)Cl>[CH:14]([C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[O:7][C@H:6]([CH3:13])[CH2:5]2)=[CH2:15]

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of (3R)-6-bromo-3-methyl-3,4-dihydro-1H-isochromen-1-one (2.4 g, 10.0 mmol) and triethylamine (2.8 ml, 19.9 mmol) in EtOH (40 ml) was added to a microwave vial containing commercially available Cl2Pd(dppf)2-DCM (0.41 g, 0.50 mmol) and potassium vinyltrifluoroborate (2.0 g, 15 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 (3R)-6-ethenyl-3-methyl-3,4-dihydro-1H-isochromen-1-one.

Workup

temperaturewas cooled
washwashed with aqueous ammonium chloride (25 mL)
dry with materialThe organic layer was then dried over magnesium sulfate
filtrationfiltered
customthe solvent was evaporated under reduced pressure
customMPLC purification (15-60% EtOAc/Hex)

Sources & evidence

ORD record: ord-5db3a127f4a749658eeb5ccc35a2bc11
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09139585B2

Reaction notes

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