Tetrahydrofuran → HCID 69073588, compound

HRID 1869972Notes

Reaction equation

HRID 1869972 reaction equation
[CH3:1][C:2]1([CH3:19])[C:11]2[C:6](=[C:7]([O:14][CH:15]([CH3:17])[CH3:16])[CH:8]=[C:9]([C:12]#[CH:13])[CH:10]=2)[C:5](=[O:18])[CH2:4][CH2:3]1.[CH3:20][O:21][C:22](=[O:31])[CH2:23][C:24]1[CH:29]=[CH:28][C:27](I)=[CH:26][CH:25]=1.C(N(CC)CC)C.O1CCCC1>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.C(OCC)(=O)C>[CH3:20][O:21][C:22](=[O:31])[CH2:23][C:24]1[CH:25]=[CH:26][C:27]([C:13]#[C:12][C:9]2[CH:8]=[C:7]([O:14][CH:15]([CH3:16])[CH3:17])[C:6]3[C:5](=[O:18])[CH2:4][CH2:3][C:2]([CH3:1])([CH3:19])[C:11]=3[CH:10]=2)=[CH:28][CH:29]=1

Participants

9

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 10378700Methyl 4-IodophenylacetateHCID 86600192HCID 86600192, compound2×

Product 1

HCID 69073588HCID 69073588, compound

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Following General Procedure B and using 4,4-dimethyl-6-ethynyl-8-(2-propoxy)-3,4-dihydro-2H-naphthalen-1-one (Intermediate 127, 0.075 g, 0.29 mmol), 4-iodo phenyl acetic acid methyl ester (0.081 g, 0.29 mmol), triethyl amine (8 mL), tetrahydrofuran (3 mL), copper(I)iodide (0.019 g, 0.1 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.07 g, 0.1 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 (0.07 g, 64%).

Sources & evidence

ORD record
ord-40615619a62f49a5a1b12b392966d24b
Source dataset
uspto-grants-2009_12
Patent number
US07638648B2

Reaction notes

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