Tetrahydrofuran → 4-(8-Cycloproply-2,2,4,4-tetramethyl-chroman-6-yl-ethynyl)-benzoic acid ethyl ester

HRID 51669

Reaktionsgleichung

Reaktionsgleichung von HRID 51669
[CH:1]1([C:4]2[CH:5]=[C:6]([C:18]#[CH:19])[CH:7]=[C:8]3[C:13]=2[O:12][C:11]([CH3:15])([CH3:14])[CH2:10][C:9]3([CH3:17])[CH3:16])[CH2:3][CH2:2]1.C(O)(=O)C1C=CC=CC=1.[CH2:29]([O:31][C:32](=[O:40])[C:33]1[CH:38]=[CH:37][C:36](I)=[CH:35][CH:34]=1)[CH3:30].C(N(CC)CC)C.O1CCCC1>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.C(OCC)(=O)C>[CH2:29]([O:31][C:32](=[O:40])[C:33]1[CH:38]=[CH:37][C:36]([C:19]#[C:18][C:6]2[CH:7]=[C:8]3[C:13](=[C:4]([CH:1]4[CH2:3][CH2:2]4)[CH:5]=2)[O:12][C:11]([CH3:14])([CH3:15])[CH2:10][C:9]3([CH3:17])[CH3:16])=[CH:35][CH:34]=1)[CH3:30]

Komponenten

9

Edukt 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 225690068-Cyclopropyl-6-ethynyl-2,2,4,4-tetramethylchroman2×HCID 69887287Ethyl-4-iodo-benzoate benzoate2×

Produkt 1

HCID 695480714-(8-Cycloproply-2,2,4,4-tetramethyl-chroman-6-yl-ethynyl)-benzoic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 8058HexaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Following general procedure F and using 8-cyclopropyl-6-ethynyl-2,2,4,4-tetramethylchroman (Intermediate 34, 0.1 g, 0.38 mmol), ethyl-4-iodo-benzoate benzoate (Reagent A, 0.1 g, 0.34 mmol), triethyl amine (5 mL), tetrahydrofuran(10 mL), copper(I)iodide(0.025 g, 0.13 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.075 g, 0.11 mmol) followed by flash column chromatography over silica gel (230-400 mesh) using 5-10% ethyl acetate in hexane as the eluent, the title compound was obtained (0.135 g, 89%).

Quellen und Nachweise

ORD-Eintrag
ord-f6ae20a07c4d46bcac2d646c87f0d300
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713647B2

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