Triethylamine → (E)-3-{4-[8-Cyclopropyl-3,4-dimethylspiro[2H-1-benzopyran-2,1'-cyclopropane]-6-yl]ethynyl-phenyl}-2-methyl-acrylic acid ethyl ester

HRID 2377315Notes

Reaction equation

HRID 2377315 reaction equation
[CH:1]1([C:4]2[C:15]3[O:14][C:11]4([CH2:13][CH2:12]4)[CH2:10][C:9]([CH3:17])(C)[C:8]=3[CH:7]=[C:6]([C:18]#[CH:19])[CH:5]=2)[CH2:3][CH2:2]1.[CH2:20]([O:22][C:23](=[O:34])/[C:24](/[CH3:33])=[CH:25]/[C:26]1[CH:31]=[CH:30][C:29](I)=[CH:28][CH:27]=1)[CH3:21].[CH2:35](N(CC)CC)C>[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>[CH2:20]([O:22][C:23](=[O:34])/[C:24](/[CH3:33])=[CH:25]/[C:26]1[CH:31]=[CH:30][C:29]([C:19]#[C:18][C:6]2[CH:5]=[C:4]([CH:1]3[CH2:3][CH2:2]3)[C:15]3[O:14][C:11]4([CH2:12][CH2:13]4)[C:10]([CH3:35])=[C:9]([CH3:17])[C:8]=3[CH:7]=2)=[CH:28][CH:27]=1)[CH3:21]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 225689518-Cyclopropyl-6-ethynyl-3 4-dihydro-4,4-dimethylspiro[2H-1-benzopyran-2,1'-cvclopropane]HCID 57424206(E)-3-(4-Iodo-phenyl)-2-methyl-acrylic acid ethyl ester2×

Product 1

HCID 69069630(E)-3-{4-[8-Cyclopropyl-3,4-dimethylspiro[2H-1-benzopyran-2,1'-cyclopropane]-6-yl]ethynyl-phenyl}-2-methyl-acrylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalyst

Procedure

Following General Procedure B and using 8-cyclopropyl-6-ethynyl-3,4-dihydro-4,4-dimethylspiro[2H-1-benzopyran-2,1′-cyclopropane] (0.077 g, 0.3 mmol), (E)-3-(4-iodo-phenyl)-2-methyl-acrylic acid ethyl ester (Reagent 7, 0.106 g, 0.23 mmol), triethyl amine (3 mL), copper(I)iodide (0.029 g, 0.15 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.064 g, 0.09 mmol) followed by flash column chromatography over silica gel (230-400 mesh), the title compound was obtained (0.06 g, 45%).

Sources & evidence

ORD record
ord-cd682e9518cd4e8fbd6f8a9a164e8f44
Source dataset
uspto-grants-2008_12
Patent number
US07468391B2

Reaction notes

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