Diethylamine → HCID 68481571, compound

HRID 1191560Notes

Reaction equation

HRID 1191560 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH3:15])=[C:10]([CH:16]3[C:21](=[O:22])[C:20]([CH3:24])([CH3:23])[O:19][C:18]([CH3:26])([CH3:25])[C:17]3=[O:27])[CH:9]=2)=[CH:4][CH:3]=1.[CH3:28][Si:29]([C:32]#[CH:33])([CH3:31])[CH3:30].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(NCC)C>CN(C)C=O.[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>[CH2:14]([C:11]1[CH:12]=[CH:13][C:8]([C:5]2[CH:4]=[CH:3][C:2]([C:33]#[C:32][Si:29]([CH3:31])([CH3:30])[CH3:28])=[CH:7][CH:6]=2)=[CH:9][C:10]=1[CH:16]1[C:21](=[O:22])[C:20]([CH3:24])([CH3:23])[O:19][C:18]([CH3:25])([CH3:26])[C:17]1=[O:27])[CH3:15]

Participants

8

Reactant 4

HCID 8021DiethylamineHCID 11776TriphenylphosphineHCID 66111TrimethylsilylacetyleneHCID 68488284HCID 68488284, compound

Product 1

HCID 68481571HCID 68481571, compoundYield 76.2%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 4-(4′-iodo-4-ethyl-biphenyl-3-yl)-2,2,6,6-tetramethylpyran-3,5-dione (0.200 g, 0.42 mmol), trimethylsilylacetylene (0.10 ml, 0.47 mmol), copper(I) iodide (4 mg, 0.023 mmol), bis(triphenylphosphine)palladium(II) chloride (0.016 g, 0.023 mmol), triphenylphosphine (0.022 g, 0.084 mmol) and diethylamine (0.65 ml) in anhydrous N,N-dimethylformamide (0.25 ml) is heated at 120° C. under microwave irradiation for 25 minutes. This mixture is then allowed to cool to room temperature and filtered through diatomaceous earth (additional washing with dichloromethane). The solvent is removed under reduced pressure and the residue is purified by flash column chromatography on silica gel (hexane/ethyl acetate 9:1 to 3:1 ratio) to yield 4-[4-ethyl-4′-(trimethylsilylethynyl)biphenyl-3-yl]-2,2,6,6-tetramethylpyran-3,5-dione (0.143 g) as a white solid which is used without further purification in the next step.

Workup

  1. temperatureto cool to room temperature
  2. filtrationfiltered through diatomaceous earth (additional washing with dichloromethane)
  3. customThe solvent is removed under reduced pressure
  4. customthe residue is purified by flash column chromatography on silica gel (hexane/ethyl acetate 9:1 to 3:1 ratio)

Sources & evidence

ORD record
ord-562b8e09bb404d369e20e54bcdcf8cdf
Source dataset
uspto-grants-2014_03
Patent number
US08680012B2

Reaction notes

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