Triethylamine → HCID 60029385, compound

HRID 1869992Notes

Reaction equation

HRID 1869992 reaction equation
[C:1]([C:5]1[C:6]([O:16][CH:17]([CH3:19])[CH3:18])=[C:7]([C:10]([CH3:15])=[C:11]([C:13]#[CH:14])[CH:12]=1)[CH:8]=[O:9])([CH3:4])([CH3:3])[CH3:2].[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.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>[CH3:20][O:21][C:22](=[O:31])[CH2:23][C:24]1[CH:25]=[CH:26][C:27]([C:14]#[C:13][C:11]2[CH:12]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[C:6]([O:16][CH:17]([CH3:19])[CH3:18])=[C:7]([CH:8]=[O:9])[C:10]=2[CH3:15])=[CH:28][CH:29]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 10378700Methyl 4-IodophenylacetateHCID 211071573-tert-Butyl-5-ethynyl-2-isopropoxy-6-methyl-benzaldehyde2×

Product 1

HCID 60029385HCID 60029385, 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 3-tert-butyl-5-ethynyl-2-isopropoxy-6-methyl-benzaldehyde (Intermediate 143, 0.35 g, 1.35 mmol), 4-iodo phenyl acetic acid methyl ester (0.374 g, 1.35 mmol), triethyl amine (8 mL), copper(I)iodide (0.02 g, 0.1 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.072 g, 0.1 mmol) followed by flash column chromatography over silica gel (230-400 mesh) using 3-5% ethyl acetate in hexane as the eluent, the title compound was obtained as a white solid (0.37 g, 75%).

Sources & evidence

ORD record
ord-1a3d5c9d332d45c1ae3e5e4265bf32af
Source dataset
uspto-grants-2009_12
Patent number
US07638648B2

Reaction notes

Loading…