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

HRID 1501945

Reaction equation

HRID 1501945 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.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(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

7

Reactant 3

HCID 8471TriethylamineHCID 23679353Potassium vinyltrifluoroborateHCID 71270763(3R)-6-bromo-3-methyl-3,4-dihydro-1H-isochromen-1-one

Product 1

HCID 86727028(3R)-6-ethenyl-3-methyl-3,4-dihydro-1H-isochromen-1-one

Reagents, catalysts & solvents 3

HCID 178418807HCID 178418807, compoundCatalystHCID 702EthanolSolventHCID 6212ChloroformSolvent

Conditions

Temperature
100 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-75f27879dd2c4c20a5a8b4bb2c8a7392
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Linked notes

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