Toluene → 5-vinyl-2,3-dihydro-1H-inden-1-one

HRID 1502968Notes

Reaction equation

HRID 1502968 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH2:6][CH2:5]2.C([O-])([O-])=O.[K+].[K+].[C:18]1(C)C=CC=C[CH:19]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:18]([C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH2:6][CH2:5]2)=[CH2:19]

Participants

5

Reactant 3

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 5206955-Bromo-1-indanone

Product 1

HCID 671719145-vinyl-2,3-dihydro-1H-inden-1-oneYield 48%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
25 °C

Procedure

To a stirred solution of 5-bromo-2,3-dihydro-1H-inden-1-one (5 g, 23.7 mmol) in toluene were added vinylboronic anhydride pyridine complex (8.55 g, 35.54 mmol), Pd(PPh3)4 (0.1 g, 0.094 mmol), K2CO3 (22.88 g, 165.83 mmol). The resultant reaction mixture was heated at reflux for 16 h. The reaction mixture was cooled to 25° C. and filtered, and the filtrate was concentrated under reduced pressure. The residue was diluted with EtOAc and washed with water and brine. The combined organic extracts were dried over anhydrous Na2SO4 and concentrated under reduced pressure. The obtained residue was purified by flash column chromatography (SiO2, 5% EtOAc in petroleum ether) afforded the title compound as a solid (1.8 g, 48%): 1H NMR (400 MHz, CDCl3) δ 7.74 (d, J=7.2 Hz, 1H), 7.49 (br s, 1H), 7.44 (d, J=7.2 Hz, 1H), 6.82 (m, 1H), 5.90 (d, J=7.4 Hz, 1H), 5.42 (d, J=6.4 Hz, 1H), 3.20 (m, 2H), 2.70 (m, 2H); ESIMS m/z 159.06 ([M+H]).

Workup

  1. customThe resultant reaction mixture
  2. temperaturewas heated
  3. temperatureat reflux for 16 h
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. additionThe residue was diluted with EtOAc
  7. washwashed with water and brine
  8. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
  9. concentrationconcentrated under reduced pressure
  10. customThe obtained residue was purified by flash column chromatography (SiO2, 5% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-dc95b16eaf95481abcdf430a7e445ec2
Source dataset
uspto-grants-2015_12
Patent number
US09211281B2

Reaction notes

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