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

HRID 426754Notes

Reaction equation

HRID 426754 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 6348Carbon DisulfideSolvent2×

Procedure

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 31 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.

Workup

  1. customheld at 31 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.

Sources & evidence

ORD record
ord-a327c865c3ef4926bbffd2c85a7c72a0
Source dataset
uspto-grants-1979_10
Patent number
US04171371

Reaction notes

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