Diisopropylethylamine → Benzyl 4-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamido)benzoate

HRID 2365466

Reaktionsgleichung

Reaktionsgleichung von HRID 2365466
[NH2:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])=[CH:4][CH:3]=1.[CH3:18][C:19]1([CH3:35])[C:23]([CH3:25])([CH3:24])[O:22][B:21]([C:26]2[CH:27]=[C:28]([CH:32]=[CH:33][CH:34]=2)[C:29](Cl)=[O:30])[O:20]1.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[CH3:24][C:23]1([CH3:25])[C:19]([CH3:18])([CH3:35])[O:20][B:21]([C:26]2[CH:27]=[C:28]([CH:32]=[CH:33][CH:34]=2)[C:29]([NH:1][C:2]2[CH:17]=[CH:16][C:5]([C:6]([O:8][CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[O:7])=[CH:4][CH:3]=2)=[O:30])[O:22]1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 98488Benzyl p-aminobenzoateHCID 578564183-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzoyl chloride

Produkt 1

HCID 57856434Benzyl 4-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamido)benzoateAusbeute 41,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of benzyl 4-aminobenzoate (4.39 g, 19.3 mmol), 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoyl chloride (4.30 g, 16.1 mmol) and N,N-diisopropylethylamine (7.49 g, 57.9 mmol) in methylene chloride (50 mL) was stirred at ambient temperature for 13 h. After this time, the reaction was concentrated under reduced pressure and purified by chromatography (silica, heptane to 1:3 ethyl acetate/heptane) to afford benzyl 4-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamido)benzoate (3.07 g, 78% pure by mass, 27% yield) as a light yellow sticky foam that was used without further purification.

Aufarbeitung

  1. concentrationAfter this time, the reaction was concentrated under reduced pressure
  2. custompurified by chromatography (silica, heptane to 1:3 ethyl acetate/heptane)

Quellen und Nachweise

ORD-Eintrag
ord-d32ee1df83364dea9f27d43ca4b51ee4
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08697699B2

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