Triethylamine → HCID 69072819, compound

HRID 2377391Notes

Reaction equation

HRID 2377391 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([O:13][CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[CH:12]=1)[C:9](=[O:22])[CH2:8][CH2:7][C:6]2([CH3:24])[CH3:23])#[CH:2].[CH3:25][O:26][C:27](=[O:36])[CH2:28][C:29]1[CH:34]=[CH:33][C:32](I)=[CH:31][CH:30]=1.C(N(CC)CC)C.C(OCC)(=O)C>CCCCCC.[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>[CH3:25][O:26][C:27](=[O:36])[CH2:28][C:29]1[CH:30]=[CH:31][C:32]([C:2]#[C:1][C:3]2[CH:12]=[C:11]([O:13][CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:20])([CH3:19])[CH3:21])[C:10]3[C:9](=[O:22])[CH2:8][CH2:7][C:6]([CH3:24])([CH3:23])[C:5]=3[CH:4]=2)=[CH:33][CH:34]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 10378700Methyl 4-IodophenylacetateHCID 21107227HCID 21107227, compound2×

Product 1

HCID 69072819HCID 69072819, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8058HexaneSolvent

Procedure

Following General Procedure B and using 6-ethynyl-4,4-dimethyl-8-(2-trimethylsilanyl-ethoxymethoxy)-3,4-dihydro-2H-naphthalen-1-one (Intermediate 73, 1.28 g, 3.7 mmol), 4-iodo phenyl acetic acid methyl ester (1.02 g, 3.7 mmol), triethyl amine (30 mL), copper(I)iodide (0.095 g, 0.5 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.35 g, 0.5 mmol) followed by flash column chromatography over silica gel (230-400 mesh) using 5-15% ethyl acetate in hexane as the eluent, the title compound was obtained as a yellow oil (1.61 g, 88%).

Sources & evidence

ORD record
ord-9151648be930475db645d2b72bda75a3
Source dataset
uspto-grants-2008_12
Patent number
US07468391B2

Reaction notes

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