8-Cyclopropyl-4,4-dimethyl-6-ethynyl-1-tetralone → 3-[4-(4-Cyclopropyl-8,8-dimethyl-5-oxo-5,6,7,8-tetrahydro-naphthalen-2-ylethynyl)-phenyl]-acrylic acid ethyl ester

HRID 2377487Notes

Reaction equation

HRID 2377487 reaction equation
[CH:1]1([C:4]2[CH:5]=[C:6]([C:17]#[CH:18])[CH:7]=[C:8]3[C:13]=2[C:12](=[O:14])[CH2:11][CH2:10][C:9]3([CH3:16])[CH3:15])[CH2:3][CH2:2]1.[CH2:19]([O:21][C:22](=[O:32])/[CH:23]=[CH:24]/[C:25]1[CH:30]=[CH:29][C:28](I)=[CH:27][CH:26]=1)[CH3:20]>[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(N(CC)CC)C>[CH2:19]([O:21][C:22](=[O:32])[CH:23]=[CH:24][C:25]1[CH:30]=[CH:29][C:28]([C:18]#[C:17][C:6]2[CH:5]=[C:4]([CH:1]3[CH2:3][CH2:2]3)[C:13]3[C:12](=[O:14])[CH2:11][CH2:10][C:9]([CH3:15])([CH3:16])[C:8]=3[CH:7]=2)=[CH:27][CH:26]=1)[CH3:20]

Participants

6

Reactant 2

HCID 211072418-Cyclopropyl-4,4-dimethyl-6-ethynyl-1-tetralone2×HCID 21107276(E)-ethyl 3-(4-iodophenyl)acrylate

Product 1

HCID 690726533-[4-(4-Cyclopropyl-8,8-dimethyl-5-oxo-5,6,7,8-tetrahydro-naphthalen-2-ylethynyl)-phenyl]-acrylic acid ethyl ester

Reagents, catalysts & solvents 3

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

Procedure

Following General Procedure B and using 8-cyclopropyl-4,4-dimethyl-6-ethynyl-1-tetralone (Intermediate 160, 0.1 g, 0.42 mmol), (E)-3-(4-iodo-phenyl)-acrylic acid ethyl ester (0.13 g, 0.42 mmol), triethyl amine (1 mL), copper(I)iodide (0.02 g, 0.1 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.070 g, 0.1 mmol) followed by flash column chromatography over silica gel (230-400 mesh), the title compound was obtained (0.12 g, 69%).

Sources & evidence

ORD record
ord-073308a584e6414c91ffc26324a0742d
Source dataset
uspto-grants-2008_12
Patent number
US07468391B2

Reaction notes

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