Triethylamine → 2-[4-(2,2-Diethyl-8-isopropyl-4,4-dimethyl-chroman-6-ylethynyl)-phenyl]-2-methyl-propionic acid methyl ester

HRID 2377348Notes

Reaction equation

HRID 2377348 reaction equation
[CH2:1]([C:3]1([CH2:20][CH3:21])[CH2:12][C:11]([CH3:14])([CH3:13])[C:10]2[C:5](=[C:6]([CH:17]([CH3:19])[CH3:18])[CH:7]=[C:8]([C:15]#[CH:16])[CH:9]=2)[O:4]1)[CH3:2].[CH3:22][O:23][C:24](=[O:53])[C:25]([C:28]1[CH:33]=[CH:32][C:31](C#CC2C=C(C3CC3)C3OC4(CC4)CC(C)(C)C=3C=2)=[CH:30][CH:29]=1)([CH3:27])[CH3:26].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>[CH3:22][O:23][C:24](=[O:53])[C:25]([C:28]1[CH:29]=[CH:30][C:31]([C:16]#[C:15][C:8]2[CH:9]=[C:10]3[C:5](=[C:6]([CH:17]([CH3:19])[CH3:18])[CH:7]=2)[O:4][C:3]([CH2:1][CH3:2])([CH2:20][CH3:21])[CH2:12][C:11]3([CH3:14])[CH3:13])=[CH:32][CH:33]=1)([CH3:27])[CH3:26]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 59856227HCID 59856227, compound2×HCID 690773412-{4-[(8-Cyclopropyl-3,4-dihydro-4,4-dimethylspiro[2H-1-benzopyran-2,1'-cyclopropane]-6-yl)ethynyl]-phenyl}-2-methyl-propionic acid methyl ester2×

Product 1

HCID 690761702-[4-(2,2-Diethyl-8-isopropyl-4,4-dimethyl-chroman-6-ylethynyl)-phenyl]-2-methyl-propionic acid methyl ester

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 2,2-diethyl-6-ethynyl-8-isopropyl-4,4-dimethyl chroman (Intermediate 29, 0.069 g, 0.24 mmol), methyl-2-(4-iodophenyl)-2-methyl-propionate (Reagent 2, 0.146 g, 0.48 mmol), triethyl amine (3 mL), copper(I)iodide (0.025 g, 0.13 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.075 g, 0.107 mmol) followed by flash column chromatography over silica gel (230-400 mesh) using 5% ethyl acetate in hexane as the eluent, the title compound was obtained as a yellow oil (0.070 g, 62%).

Sources & evidence

ORD record
ord-eb11b3eb2e1b492e81f6a85fd2ded4db
Source dataset
uspto-grants-2008_12
Patent number
US07468391B2

Reaction notes

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