6-Ethynyl-8-isopropyl-2,2,4,4-tetramethylchroman → 3-[3-(8-Isopropyl-2,2,4,4-tetramethyl-chroman-6-ylethynyl)phenyl]-acrylic acid ethyl ester

HRID 1869870

Reaktionsgleichung

Reaktionsgleichung von HRID 1869870
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([CH:13]([CH3:15])[CH3:14])[CH:12]=1)[O:9][C:8]([CH3:17])([CH3:16])[CH2:7][C:6]2([CH3:19])[CH3:18])#[CH:2].[CH2:20]([O:22][C:23](=[O:33])[CH:24]=[CH:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28](I)[CH:27]=1)[CH3:21]>[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.C(N(CC)CC)C>[CH2:20]([O:22][C:23](=[O:33])[CH:24]=[CH:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([C:2]#[C:1][C:3]2[CH:4]=[C:5]3[C:10](=[C:11]([CH:13]([CH3:14])[CH3:15])[CH:12]=2)[O:9][C:8]([CH3:17])([CH3:16])[CH2:7][C:6]3([CH3:18])[CH3:19])[CH:27]=1)[CH3:21]

Komponenten

6

Edukt 2

HCID 211072306-Ethynyl-8-isopropyl-2,2,4,4-tetramethylchroman2×HCID 545009022-Propenoic acid, 3-(3-iodophenyl)-, ethyl ester

Produkt 1

HCID 690717073-[3-(8-Isopropyl-2,2,4,4-tetramethyl-chroman-6-ylethynyl)phenyl]-acrylic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

Following General Procedure B and using 6-ethynyl-8-isopropyl-2,2,4,4-tetramethylchroman (Intermediate 32, 0.05 g, 0.2 mmol), ethyl-3-iodo cinnamate (Reagent 6, 0.118 g, 0.39 mmol), triethyl amine (2 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), the title compound was obtained (0.058 g, 69%).

Quellen und Nachweise

ORD-Eintrag
ord-6b2dfe8bbfc44d82a1c36844387cfb61
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07638648B2

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