Dimethyl acetylenedicarboxylate → HCID 14994872, compound

HRID 2248356Notes

Reaction equation

HRID 2248356 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][CH:10]=[CH:11][CH:12]=2)=[CH:4][CH:3]=1.[C:13]([C:19]([O:21][CH3:22])=[O:20])#[C:14][C:15]([O:17][CH3:18])=[O:16]>O.CCOC(C)=O.[Pt]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]23[O:9][CH:10]([CH2:11][CH2:12]2)[C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:13]3[C:19]([O:21][CH3:22])=[O:20])=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 12980Dimethyl acetylenedicarboxylateHCID 10965101HCID 10965101, compound

Product 1

HCID 14994872HCID 14994872, compound

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-(4-Chlorophenylfuran (2.3 g) and dimethyl acetylenedicarboxylate (1.54 ml) were subjected to Diels-Alder reaction in water (5.48 ml) as described in Example 53. The resulting adduct was dissolved in EtOAc (140 ml) and hydrogenated over Adam's platinum catalyst (100 mg) at room temperature and atmospheric pressure. The uptake of one equivalent of H2 required about 3 hours. The catalyst was removed by filtration and the solvent removed in-vacuo to provide a gummy product which was chromatographed over silica gel column. Elution of column with 10% acetone in n-hexane gave fractions containing the pure title compound (3.25 g) as colorless crystals:m.p. 90°-91° C.; PMR δH (CDCl3): 1.55-1.7 (n,1H), 2-2.3 (m,3H), 3.62 (s,3H), 3.79(s,3H), 5.37 (d, 1H, J=4.2 Hz), 7.3-7.44 (m,4H).

Workup

  1. customabout 3 hours
  2. customThe catalyst was removed by filtration
  3. customthe solvent removed in-vacuo
  4. customto provide a gummy product which
  5. customwas chromatographed over silica gel column
  6. washElution of column with 10% acetone in n-hexane
  7. customgave fractions

Sources & evidence

ORD record
ord-ac571849fd7b467ebcff59c0625aa981
Source dataset
uspto-grants-1991_08
Patent number
US05039676

Reaction notes

Loading…