Phenyl chloroformate → 5-[2-(3-Chloro-phenyl)-ethoxy]-4-ethyl-4H-pyridine-1,3-dicarboxylic acid 3-ethyl ester 1-phenyl ester

HRID 1475763

Reaktionsgleichung

[CH2:1]([O:3][C:4](=[O:21])[C:5]1[CH:10]=[C:9]([O:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=2)[CH:8]=[N:7][CH:6]=1)[CH3:2].Cl[C:23]([O:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:24].[CH2:32]([Mg]Br)[CH3:33]>C1COCC1>[C:26]1([O:25][C:23]([N:7]2[CH:8]=[C:9]([O:11][CH2:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=3)[CH:10]([CH2:32][CH3:33])[C:5]([C:4]([O:3][CH2:1][CH3:2])=[O:21])=[CH:6]2)=[O:24])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Komponenten

Reaktionsbedingungen

Temperatur: -30 °C

Versuchsvorschrift

The compound of step 1 (100 mg, 0.327 mmol) was dissolved in THF (1.5 ml) and the mixture was cooled to −30° C. Phenyl chloroformate (77.6 mg, 0.49 mmol) was added and the mixture was stirred for 10 minutes. Ethyl magnesiumbromide (0.589 ml, 1M in THF) was added at −30° C. and the mixture was stirred for 30 minutes, partitioned between diethylether and aqueous ammonium chloride solution, the combined organic extracts were dried over sodium chloride and evaporated to dryness in vacuo. The raw material was purified by silica gel chromatography with a heptane/ethyl acetate gradient to yield the title compound (84 mg).

Aufarbeitung

stirringthe mixture was stirred for 30 minutes
custompartitioned between diethylether and aqueous ammonium chloride solution
dry with materialthe combined organic extracts were dried over sodium chloride
customevaporated to dryness in vacuo
customThe raw material was purified by silica gel chromatography with a heptane/ethyl acetate gradient

Quellen und Nachweise

ORD-Eintrag: ord-d1301782727445229f960c00152ae8af
Quelldatensatz: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09018383B2

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