Triethylamine → HCID 57450636, compound

HRID 2377384Notes

Reaction equation

HRID 2377384 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([OH:13])[CH:12]=1)[C:9](=[O:14])[CH2:8][CH2:7][C:6]2([CH3:16])[CH3:15])#[CH:2].[CH3:17][O:18][C:19](=[O:28])[CH2:20][C:21]1[CH:26]=[CH:25][C:24](I)=[CH:23][CH:22]=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>[CH3:17][O:18][C:19](=[O:28])[CH2:20][C:21]1[CH:22]=[CH:23][C:24]([C:2]#[C:1][C:3]2[CH:12]=[C:11]([OH:13])[C:10]3[C:9](=[O:14])[CH2:8][CH2:7][C:6]([CH3:16])([CH3:15])[C:5]=3[CH:4]=2)=[CH:25][CH:26]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 10378700Methyl 4-IodophenylacetateHCID 21107229HCID 21107229, compound2×

Product 1

HCID 57450636HCID 57450636, 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-8-hydroxy-4,4-dimethyl-3,4-dihydro-2H-naphthalen-1-one (Intermediate 67, 1.58 g, 7.4 mmol), 4-iodo phenyl acetic acid methyl ester (2.2 g, 7.94 mmol), triethyl amine (12 mL), copper(I)iodide (0.38 g, 1.99 mmol) and dichlorobis(triphenylphosphine)palladium(II) (1.2 g, 1.71 mmol) followed by flash column chromatography over silica gel (230-400 mesh) using 16% ethyl acetate in hexane as the eluent, the title compound was obtained as a yellow oil (2.1 g, 78%).

Sources & evidence

ORD record
ord-46144c2e13654299a05eaf8ccee8859b
Source dataset
uspto-grants-2008_12
Patent number
US07468391B2

Reaction notes

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