Methyl chloroacetate → HCID 67267336, Verbindung

HRID 602751

Reaktionsgleichung

Reaktionsgleichung von HRID 602751
[C:1]1(S)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+].[CH3:18][O:19][C:20](=[O:23])[CH2:21]Cl.O[O:25][S:26]([O-:28])=O.[K+]>CC(=O)C>[CH3:18][O:19][C:20](=[O:23])[CH2:21][S:26]([C:9]1[C:10]2[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=2)[CH:6]=[CH:7][CH:8]=1)(=[O:28])=[O:25]

Komponenten

6

Edukt 4

HCID 7295Methyl chloroacetateHCID 11430Potassium CarbonateHCID 682591-NaphthalenethiolHCID 23707502Potassium hydroxy sulfite

Produkt 1

HCID 67267336HCID 67267336, VerbindungAusbeute 55,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a stirred suspension of 3.1 g (0.019 mol) of naphthalene-1-thiol and 2.94 g (0.021 mol, 1.1 eq) of K2CO3 in 100 mL of propan-2-one cooled at 0° C., 3.15 g (0.029 mol, 1.5 eq) of chloro-acetic acid methyl ester were added in one portion. The ice bath was removed and the reaction mixture was stirred an additional 4 hours. The reaction was filtered, the solvent evaporated and the resulting residue was taken up in 100 mL of MeOH. 14.3 g (0.023 mol, 1.2 eq) of oxone (potassium peroxymonosulfate) were added and the reaction mixture was stirred over night at RT. The salts were filtered off, the solvent evaporated and the residue purified by column chromatography on silica gel with heptane/EtOAc (from 4:1 to 1:2) to afford 2.78 g (55%) of (naphthalene-1-sulfonyl)-acetic acid methyl ester as a light yellow oil, MS: 265 (MH+).

Aufarbeitung

  1. customThe ice bath was removed
  2. filtrationThe reaction was filtered
  3. customthe solvent evaporated
  4. stirringthe reaction mixture was stirred over night at RT
  5. filtrationThe salts were filtered off
  6. customthe solvent evaporated
  7. customthe residue purified by column chromatography on silica gel with heptane/EtOAc (from 4:1 to 1:2)

Quellen und Nachweise

ORD-Eintrag
ord-8b117963bb6648eeb711e6a3174dc962
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07906546B2

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