Ethyl 2-furoate → Ethyl 5-(3,4-methylenedioxybenzyl)-2-furoate

HRID 262209

Reaktionsgleichung

Reaktionsgleichung von HRID 262209
[CH2:1]1[O:11][C:10]2[CH:9]=[CH:8][C:5]([CH2:6]Br)=[CH:4][C:3]=2[O:2]1.[O:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[C:17]([O:19][CH2:20][CH3:21])=[O:18]>[Cl-].[Zn+2].[Cl-].C(=S)=S>[CH2:1]1[O:11][C:10]2[CH:9]=[CH:8][C:5]([CH2:6][C:16]3[O:12][C:13]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:14][CH:15]=3)=[CH:4][C:3]=2[O:2]1

Komponenten

5

Edukt 2

HCID 11980Ethyl 2-furoateHCID 64514231,3-Benzodioxole, 5-(bromomethyl)-

Produkt 1

HCID 20389920Ethyl 5-(3,4-methylenedioxybenzyl)-2-furoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3007855ZincchlorideKatalysatorHCID 6348Carbon DisulfideLösungsmittel2×

Versuchsvorschrift

A solution of 60 g. of 3,4-methylenedioxybenzyl bromide in 200 ml. of carbon disulfide was slowly added over a period of 45 minutes to a solution of 260 g. of ethyl 2-furoate and 20 g. of zinc chloride in 600 ml. of carbon disulfide held at -10° C. The reaction mixture was allowed to warm to room temperature, filtered, extracted with water and saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was removed and the residue distilled to give 27 g. of ethyl 5-(3,4-methylenedioxybenzyl)-2-furoate, b.p. 162°-166° C. (0.5 mm), which crystallized to a solid, m.p. 67°-68° C.

Aufarbeitung

  1. customheld at -10° C
  2. filtrationfiltered
  3. extractionextracted with water and saturated sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was removed
  6. distillationthe residue distilled
  7. customto give 27 g
  8. customof ethyl 5-(3,4-methylenedioxybenzyl)-2-furoate, b.p. 162°-166° C. (0.5 mm), which crystallized to a solid, m.p. 67°-68° C.

Quellen und Nachweise

ORD-Eintrag
ord-dad472cfeef34eba94d07703e00242a6
Quelldatensatz
uspto-grants-1979_05
Patentnummer
US04153719

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