Dimethylformamide → HCID 131733004, compound

HRID 2177400Notes

Reaction equation

HRID 2177400 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12](Br)=[C:13]2[C:17]=1[C:16](=[O:18])[CH2:15][CH2:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20]([O:24][CH2:25][CH3:26])(=[O:23])[CH:21]=[CH2:22].CCN(C(C)C)C(C)C.CN(C)C=O>O.Cl[Pd]Cl>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12](/[CH:22]=[CH:21]/[C:20]([O:24][CH2:25][CH3:26])=[O:23])=[C:13]2[C:17]=1[C:16](=[O:18])[CH2:15][CH2:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8821Ethyl AcrylateHCID 81531DiisopropylethylamineHCID 53429317HCID 53429317, compound

Product 1

HCID 131733004HCID 131733004, compound

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

Into a 100-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed 7-(benzyloxy)-4-bromo-2,3-dihydro-1H-inden-1-one (520 mg, 1.64 mmol, 1.00 equiv), ethyl prop-2-enoate (825 mg, 8.24 mmol, 5.03 equiv), PdCl2 (58 mg, 0.33 mmol, 0.200 equiv), DIEA (1.06 g, 8.20 mmol, 5.00 equiv), (o-Tol)3P (201 mg, 0.66 mmol, 0.400 equiv), N,N-dimethylformamide (15 mL). The resulting solution was stirred for overnight at 90° C. in an oil bath. The reaction progress was monitored by TLC (ethyl acetate/petroleum ether=1:2). The resulting solution was diluted with 20 mL of H2O. The resulting solution was extracted with 3×15 mL of ethyl acetate and the organic extracts were combined. The resulting mixture was washed with 1×15 mL of water and 1×15 mL of aqueous saturated sodium chloride solution. The mixture was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was applied to a silica gel column, eluting with ethyl acetate/petroleum ether (1:4). This resulted in 500 mg (86%) of ethyl (2E)-3-[7-(benzyloxy)-1-oxo-2,3-dihydro-1H-inden-4-yl]prop-2-enoate as a red solid.

Workup

  1. customInto a 100-mL round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. extractionThe resulting solution was extracted with 3×15 mL of ethyl acetate
  4. washThe resulting mixture was washed with 1×15 mL of water and 1×15 mL of aqueous saturated sodium chloride solution
  5. dry with materialThe mixture was dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. washeluting with ethyl acetate/petroleum ether (1:4)
  8. customThis resulted in 500 mg (86%) of ethyl (2E)-3-[7-(benzyloxy)-1-oxo-2,3-dihydro-1H-inden-4-yl]prop-2-enoate as a red solid

Sources & evidence

ORD record
ord-1b2047c116384ba68928122b93496afc
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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