Pyridine → 3-(Acetyloxy)-2,2-dimethylpropanoic acid

HRID 232116

Reaktionsgleichung

Reaktionsgleichung von HRID 232116
[C:1](Cl)(=[O:3])[CH3:2].N1C=CC=CC=1.[CH3:11][C:12]([CH3:18])([CH2:16][OH:17])[C:13]([OH:15])=[O:14]>CN(C1C=CN=CC=1)C.CCOCC>[C:1]([O:17][CH2:16][C:12]([CH3:18])([CH3:11])[C:13]([OH:15])=[O:14])(=[O:3])[CH3:2]

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 785483-Hydroxy-2,2-dimethylpropionic acid

Produkt 1

HCID 131926213-(Acetyloxy)-2,2-dimethylpropanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

Acetyl chloride (4.52, 58.2 mmol) was added dropwise to a cold (0° C.) pyridine solution (10 ml) of 2,2-dimethyl-3-hydroxypropionic acid (5.5 g, 46.5 mmol) and 4-DMAP (0.57 g, 4.65 mmol). After stirring overnight at ambient temperature, the reaction was poured into ether (200 ml). This mixture was washed with 10% HCl (2×20 ml), and saturated brine (2×25 ml) and the resulting ethereal solution was dried (MgSO4). Evaporation gave the title compound as a pale yellow solid which was used in the next step without further purification. NMR (CDCl3) δ 4.13 (2 H, s), 2.08 (3 H, s), 1.26 (6 H, s).

Aufarbeitung

  1. washThis mixture was washed with 10% HCl (2×20 ml), and saturated brine (2×25 ml)
  2. dry with materialthe resulting ethereal solution was dried (MgSO4)
  3. customEvaporation

Quellen und Nachweise

ORD-Eintrag
ord-a870a0c1965147ce963c177be784b19c
Quelldatensatz
uspto-grants-1989_07
Patentnummer
US04851436

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