Pivaloyl chloride → 2,2-Dimethyl-propionic acid 2-[4-(2,2-dimethyl-propionyloxy)-phenyl]-benzofuran-5-yl ester

HRID 1836033Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1836033
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][C:11]=3[CH:12]=2)=[CH:4][CH:3]=1.[C:18](Cl)(=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20]>C(Cl)Cl.N1C(=O)CC[C@H]1C(O)=O.C(Cl)Cl>[CH3:20][C:19]([CH3:22])([CH3:21])[C:18]([O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][C:14]([O:17][C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:13][C:11]=3[CH:12]=2)=[CH:4][CH:3]=1)=[O:23]

Komponenten

5

Edukt 2

HCID 62493Pivaloyl chlorideHCID 6569362-(4-Hydroxy-phenyl)benzofuran-5-OL

Produkt 1

HCID 235173722,2-Dimethyl-propionic acid 2-[4-(2,2-dimethyl-propionyloxy)-phenyl]-benzofuran-5-yl esterAusbeute 64,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 131724524CH2Cl2 PyrLösungsmittel

Versuchsvorschrift

A solution of 75 (8.2 g, 36.3 mmol) in CH2Cl2/Pyr was treated with pivaloyl chloride (9.63 g, 79.9 mmol) and stirred at rt until TLC indicated that the reaction was complete. The reaction was worked up by diluting with additional CH2Cl2 and washing with 2 N HCl aq. The CH2Cl2 layer was washed with satd NaHCO3 aq, brine and dried over MgSO4. Filtration and concentration yielded 9.3 g of the crude solid that was used as is for the next reaction.

Aufarbeitung

  1. washwashing with 2 N HCl aq. The CH2Cl2 layer
  2. washwas washed with satd NaHCO3 aq, brine
  3. dry with materialdried over MgSO4
  4. filtrationFiltration and concentration

Quellen und Nachweise

ORD-Eintrag
ord-b6c8d2d5dfe44555a90469ff01c31b24
Quelldatensatz
uspto-grants-2004_08
Patentnummer
US06774248B2

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