Triethylamine → HCID 69072819, compound

HRID 1765779Notes

Reaction equation

HRID 1765779 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([O:13][CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[CH:12]=1)[C:9](=[O:22])[CH2:8][CH2:7][C:6]2([CH3:24])[CH3:23])#[CH:2].[CH3:25][O:26][C:27](=[O:36])[CH2:28][C:29]1[CH:34]=[CH:33][C:32](I)=[CH:31][CH:30]=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>[CH3:25][O:26][C:27](=[O:36])[CH2:28][C:29]1[CH:30]=[CH:31][C:32]([C:2]#[C:1][C:3]2[CH:12]=[C:11]([O:13][CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:20])([CH3:19])[CH3:21])[C:10]3[C:9](=[O:22])[CH2:8][CH2:7][C:6]([CH3:24])([CH3:23])[C:5]=3[CH:4]=2)=[CH:33][CH:34]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 10378700Methyl 4-IodophenylacetateHCID 21107227HCID 21107227, compound2×

Product 1

HCID 69072819HCID 69072819, 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 6-ethynyl-4,4-dimethyl-8-(2-trimethylsilanyl-ethoxymethoxy)-3,4-dihydro-2H-naphthalen-1-one (Intermediate 73, 1.28 g, 3.7 mmol), 4-iodo phenyl acetic acid methyl ester (1.02 g, 3.7 mmol), triethyl amine (30 mL), copper(I)iodide (0.095 g, 0.5 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.35 g, 0.5 mmol) followed by flash column chromatography over silica gel (230–400 mesh) using 5–15% ethyl acetate in hexane as the eluent, the title compound was obtained as a yellow oil (1.61 g, 88%).

Sources & evidence

ORD record
ord-9a235fe6219d4cda8214eb8aad8916ca
Source dataset
uspto-grants-2007_06
Patent number
US07226951B2

Reaction notes

Loading…