Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl ester → N-methyl-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetamide

HRID 1047070Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1047070
C([CH2:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([B:15]2[O:19][C:18]([CH3:21])([CH3:20])[C:17]([CH3:23])([CH3:22])[O:16]2)=[CH:11][CH:10]=1)=[O:7])(C)(C)C.[CH3:24]C(OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=O>N1C=CC=CC=1.CCOC(C)=O>[CH3:24][N:8]([C:9]1[CH:14]=[CH:13][C:12]([B:15]2[O:16][C:17]([CH3:23])([CH3:22])[C:18]([CH3:21])([CH3:20])[O:19]2)=[CH:11][CH:10]=1)[C:6](=[O:7])[CH3:5]

Komponenten

5

Edukt 2

HCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl esterHCID 67503416tert-butyl N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetamide

Produkt 1

HCID 59232387N-methyl-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetamideAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of tert-butyl N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetamide (100 mg, 0.429 mmol) in pyridine (1 mL) was added acetic anhydrate (1 mL) and stirred at room temperature for 23 hours. The mixture was diluted with AcOEt, washed with 1N HCl, brine, dried over Na2SO4, then filtrated through Celite pad. The filtrate was concentrated to afford the desired product (91 mg, 77%) as a dark brown solid. 1HNMR (CDCl3) 400 MHz δ: 7.85 (d, J=8.0 Hz, 2H), 7.19 (d, J=8.0 Hz, 2H), 3.27 (s, 3H), 1.88 (s, 3H), 1.35 (s, 12H).

Aufarbeitung

  1. washwashed with 1N HCl, brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltrated through Celite pad
  4. concentrationThe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-fdcb01d3dac143bd9504e13511b8feb8
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08569331B2

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