Potassium Carbonate → 3-vinyl-10,11-dihydro-5H-dibenzo[c,g]chromen-8(9H)-one

HRID 590648Notes

Reaction equation

HRID 590648 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[C:14]3[CH:13]=[C:12]4[CH2:15][CH2:16][CH2:17][C:18](=[O:19])[C:11]4=[CH:10][C:9]=3[O:8][CH2:7][C:6]=2[CH:20]=1.[CH:21]([B-](F)(F)F)=[CH2:22].[K+].COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.C([O-])([O-])=O.[K+].[K+]>CC([O-])=O.CC([O-])=O.[Pd+2].C(O)CC>[CH:21]([C:2]1[CH:3]=[CH:4][C:5]2[C:14]3[CH:13]=[C:12]4[CH2:15][CH2:16][CH2:17][C:18](=[O:19])[C:11]4=[CH:10][C:9]=3[O:8][CH2:7][C:6]=2[CH:20]=1)=[CH2:22]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 23679353Potassium vinyltrifluoroborateHCID 696733663-Chloro-10,11-dihydro-5H-benzo(d)naphtho(2,3-b)pyran-8(9H)-one

Product 1

HCID 696732503-vinyl-10,11-dihydro-5H-dibenzo[c,g]chromen-8(9H)-oneYield 584.1%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 10311-PropanolSolvent

Procedure

A 3-neck oven-dried 500 mL round-bottom flask was cooled under Ar, then charged with 3-Chloro-10,11-dihydro-5H-dibenzo[c,g]chromen-8(9H)-one (12.0 g, 42.1 mmol), potassium vinyltrifluoroborate (8.47 g, 6.32 mmol), Pd(OAc)2 (473 mg, 2.11 mmol), SPhos (1.74 g, 4.25 mmol), K2CO3 (17.5 g, 126 mmol) and anhydrous propanol (120 mL). The reaction mixture was sparged with Ar for 16 min, then heated to reflux for 5.5 h. Upon completion, the reaction mixture was cooled to RT and concentrated under reduced pressure. The crude residue was suspended in DCM, then washed with H2O and brine. The organic solution was dried over MgSO4, filtered and concentrated under reduced pressure. The resulting residue was further purified via silica plug, eluting with DCM to afford 3-vinyl-10,11-dihydro-5H-dibenzo[c,g]chromen-8(9H)-one (10.2 g, 87%).

Workup

  1. customA 3-neck oven-dried 500 mL round-bottom flask
  2. temperaturewas cooled under Ar
  3. customThe reaction mixture was sparged with Ar for 16 min
  4. temperatureheated
  5. temperatureto reflux for 5.5 h
  6. concentrationconcentrated under reduced pressure
  7. washwashed with H2O and brine
  8. dry with materialThe organic solution was dried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customThe resulting residue was further purified via silica plug
  12. washeluting with DCM

Sources & evidence

ORD record
ord-621014727cc74e119be7986a620d9a34
Source dataset
uspto-grants-2016_01
Patent number
US09233974B2

Reaction notes

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