Ethyl bromoacetate → Acetic acid, (p-tolylsulfonyl)-, ethyl ester

HRID 497415

Reaktionsgleichung

COC1N=C(C[S:10]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)(=[O:12])=[O:11])C([N+]([O-])=O)=CC=1.Br[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[CH2:28]([O:27][C:25](=[O:26])[CH2:24][S:10]([C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1)(=[O:12])=[O:11])[CH3:29]

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

A mixture of 5.0 g (15.5 mmol) of 6-methoxy-3-nitro-2-(toluene-4-sulfonyl methyl)-pyridine and 1.8 mL (16 mmol) of ethyl bromoacetate is dissolved in 20 mL of DMF. To this solution is added 4.4 g (32 mmol) of K2CO3 and the reaction mixture is heated to 50° C. for 18 hours. The reaction mixture is cooled to room temperature and diluted with 300 mL of water. The mixture is extracted with ethyl acetate. The ethyl acetate extracts are dried (Na2SO4) and evaporated to yield 7.2 grams of 6-methoxy-3-nitro-pyridin-2-yl]-[toluene-4-sulfonyl]-acetic acid ethyl ester. 1H NMR (CDCl3) δ 8.30 (d, 1H), 7.60 (d, 2H), 7.30 (d, 2H), 6.80 (d, 1H), 6.30 (m, 1H), 4.0 (q, 2H), 3.80 (s, 3H), 3.60 (m, 1H), 3.10 (m, 1H), 2.40 (s, 3H), 1.10 (t, 3H). Mass spectrum: m/e=409.0 (p+1). TLC (7/3: hexanes/ethyl acetate) Rf=0.5. Step 3:

Aufarbeitung

temperatureThe reaction mixture is cooled to room temperature
extractionThe mixture is extracted with ethyl acetate
dry with materialThe ethyl acetate extracts are dried (Na2SO4)
customevaporated

Quellen und Nachweise

ORD-Eintrag: ord-cb271b46556548aebf195e13a84d822a
Quelldatensatz: uspto-grants-2005_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06949562B2

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