Potassium Carbonate → methyl 1-methylidene-2,3-dihydro-1H-indene-4-carboxylate

HRID 1187040Notes

Reaction equation

HRID 1187040 reaction equation
Br[C:2]1[C:3]([CH2:12][CH2:13][CH:14]=[CH2:15])=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(#N)C>[CH2:15]=[C:14]1[C:2]2[CH:11]=[CH:10][CH:9]=[C:4]([C:5]([O:7][CH3:8])=[O:6])[C:3]=2[CH2:12][CH2:13]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 66644010Methyl 3-bromo-2-but-3-en-1-ylbenzoate

Product 1

HCID 66646307methyl 1-methylidene-2,3-dihydro-1H-indene-4-carboxylate

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
120 °C

Procedure

To a microwave tube charged with methyl 3-bromo-2-but-3-en-1-ylbenzoate (800 mg, 3.0 mmol) and a stir bar was added palladium(II) acetate (67 mg, 0.30 mmol), triphenylphosphine (310 mg, 1.19 mmol), potassium carbonate (2.46 g, 18.0 mmol), and acetonitrile (20 mL). The reaction tube was sealed, and the solution was purged three times with nitrogen, and heated in a microwave apparatus to 120° C. for 10 minutes. TLC showed a big blue spot right below the SM. The product was isolated by silica gel chromatography. LC-MS M+1 (calc. 189, found 189).

Workup

  1. customThe reaction tube was sealed
  2. customthe solution was purged three times with nitrogen
  3. customThe product was isolated by silica gel chromatography

Sources & evidence

ORD record
ord-f29717b321ce4b409c73a0ddc67e3af9
Source dataset
uspto-grants-2014_03
Patent number
US08673920B2

Reaction notes

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