Triethylamine → HCID 59692068, compound

HRID 898675Notes

Reaction equation

HRID 898675 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([CH:13]=[O:14])[CH:12]=1)[O:9][C:8]([CH3:16])([CH3:15])[CH2:7][C:6]2([CH3:18])[CH3:17])#[CH:2].[CH3:19][O:20][C:21](=[O:30])[CH2:22][C:23]1[CH:28]=[CH:27][C:26](I)=[CH:25][CH:24]=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>[CH3:19][O:20][C:21](=[O:30])[CH2:22][C:23]1[CH:24]=[CH:25][C:26]([C:2]#[C:1][C:3]2[CH:4]=[C:5]3[C:10](=[C:11]([CH:13]=[O:14])[CH:12]=2)[O:9][C:8]([CH3:16])([CH3:15])[CH2:7][C:6]3([CH3:18])[CH3:17])=[CH:27][CH:28]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 10378700Methyl 4-IodophenylacetateHCID 59692072HCID 59692072, compound2×

Product 1

HCID 59692068HCID 59692068, 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 J and using 6-ethynyl-2,2,4,4-tetramethyl chroman-8-carbaldehyde (Compound 44, 0.39 g, 1.61 mmol), 4-iodo phenyl acetic acid methyl ester (0.444 g, 1.61 mmol), triethyl amine (10 mL), copper(I)iodide (0.025 g, 0.13 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.090 g, 0.13 mmol) followed by flash column chromatography over silica gel (230-400 mesh) using 5-20% ethyl acetate in hexane as the eluent the title compound was obtained as an oil (0.5 g, 80%).

Sources & evidence

ORD record
ord-2e4df7ad403245ba8c4c148d49826043
Source dataset
uspto-grants-2008_04
Patent number
US07351737B2

Reaction notes

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