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

HRID 2173144Notes

Reaction equation

HRID 2173144 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[O:7][CH: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][CH:6]([CH3:13])[CH2:5]2)=[CH2:15]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 23679353Potassium vinyltrifluoroborateHCID 675161976-bromo-3-methyl-3,4-dihydro-1H-2-benzopyran-1-one

Product 1

HCID 675177156-ethenyl-3-methyl-3,4-dihydro-1H-isochromen-1-one

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6212ChloroformSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 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 Cl2Pd(dppf)2-DCM (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 6-ethenyl-3-methyl-3,4-dihydro-1H-isochromen-1-one.

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-f8fc1a36c2e74fa692cd9f0d2c6ac31a
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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