Methyl chloroacetate → Methyl 2-(2-methylfur-5-ylthio)acetate

HRID 1029758

Reaktionsgleichung

Reaktionsgleichung von HRID 1029758
CC1OC=CC=1.O1C=CC=C1.[Li].[CH3:13][C:14]1[O:15][C:16]([SH:19])=[CH:17][CH:18]=1.Cl[CH2:21][C:22]([O:24][CH3:25])=[O:23]>CCOCC>[CH3:13][C:14]1[O:15][C:16]([S:19][CH2:21][C:22]([O:24][CH3:25])=[O:23])=[CH:17][CH:18]=1

Komponenten

7

Edukt 5

HCID 7295Methyl chloroacetateHCID 8029FuranHCID 107972-MethylfuranHCID 1437542-Furanthiol, 5-methyl-HCID 3028194Lithium

Produkt 1

HCID 19900770Methyl 2-(2-methylfur-5-ylthio)acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

The necessary starting material was prepared from 2-methylfuran (16.4 g) by an analogous procedure to that described for furan itself in Example 14, except that in this case the intermediate lithium salt of 2-methylfuran-5-thiol was reacted in dry ether at -20° C. with methyl 2-chloroacetate. The reaction mixture was stirred for 2 days and then partitioned between water (800 ml) and ether (3×400 ml). The organic layers were dried (MgSO4) and evaporated. The residual oil was distilled to give methyl 2-(2-methylfur-5-ylthio)acetate (40.1 g) b.p. 94°-96° C./0.5 mm; NMR (90 MHz): 2.30 (s,3H), 3.45 (s,2H), 3.70 (s,3H), 5.95 (m,1H), 6.45 (d,1H).

Aufarbeitung

  1. custompartitioned between water (800 ml) and ether (3×400 ml)
  2. dry with materialThe organic layers were dried (MgSO4)
  3. customevaporated
  4. distillationThe residual oil was distilled

Quellen und Nachweise

ORD-Eintrag
ord-df3eecd0a60b492999a2d97aae41a84e
Quelldatensatz
uspto-grants-1992_04
Patentnummer
US05102905

Verknüpfte Notizen

Wird geladen…