Dimethyl acetylenedicarboxylate → HCID 14994872、化合物

HRID 2248356ノート

反応式

HRID 2248356 の反応式
[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

参加物

6

反応物 2

HCID 12980Dimethyl acetylenedicarboxylateHCID 10965101HCID 10965101、化合物

生成物 1

HCID 14994872HCID 14994872、化合物

試薬・触媒・溶媒 3

HCID 23939Platinum触媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-ac571849fd7b467ebcff59c0625aa981
出典データセット
uspto-grants-1991_08
特許番号
US05039676

反応ノート

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