Diethyl Ether → HCID 22323716, compound

HRID 2288858Notes

Reaction equation

HRID 2288858 reaction equation
[C:1]([C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH3:14])(C)[CH2:8][C:9]2=O)=C[CH:4]=1)#C.I[C:16]1[CH:26]=[CH:25][C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:18][CH:17]=1.[C:27]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC[O:48][CH2:49][CH3:50]>CCN(CC)CC.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:4][C:3]1([CH3:1])[CH2:50][C:49](=[O:48])[C:9]2[C:10]([CH:6]=[C:7]([C:14]#[C:27][C:16]3[CH:26]=[CH:25][C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:18][CH:17]=3)[CH:8]=2)=[CH:11]1

Participants

8

Reactant 4

HCID 3283Diethyl EtherHCID 11776TriphenylphosphineHCID 142891Ethyl 4-iodobenzoateHCID 22323714HCID 22323714, compound

Product 1

HCID 22323716HCID 22323716, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

A solution of 280.0 mg (1.520 mmol) 6-ethynyl-2,3- dihydro-3,3-dimethyl-1H-inden-1-one (Compound DD) and 419.6 mg (1.520 mmol) ethyl 4-iodobenzoate in 5 ml Et3N was sparged with argon for 40 minutes. To this solution was added 271.0 mg (1.033 mmol) of triphenylphosphine, 53.5 mg (0.281 mmol) of copper(I) iodide, and 53.5 mg (0.076 mmol) of bis(triphenylphosphine)palladium(II) chloride. The resulting mixture was heated to reflux for 2.5 hours, cooled to room temperature, and diluted with Et2O. After filtration through a pad of Celite, the filtrate was washed with H2O, M HCl, H2O, and saturated aqueous NaCl, then dried over MgSO4, and concentrated under reduced pressure. The title compound was isolated as a pale-yellow solid by column chromatography (15% EtOAc-hexanes). 1H NMR (300 MHz, d6-acetone): δ 8.05 (2H, d, J=8.6 Hz), 7.87 (1H, dd, J=1.4, 8.1 Hz), 7.75 (2H, m), 7.70 (2H, d, J=8.5 Hz), 4.36 (2H, q, J=7.1 Hz), 2.60 (2H, s), 1.45 (6H, s), 1.37 (3H, t, J=7.1 Hz).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 2.5 hours
  3. filtrationAfter filtration through a pad of Celite
  4. washthe filtrate was washed with H2O, M HCl, H2O, and saturated aqueous NaCl
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6d32d52cfd8d4c31bdaefaa921dac899
Source dataset
uspto-grants-2000_07
Patent number
US06090810

Reaction notes

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