Tetrahydrofuran → 3-[(5-ethoxycarbonyl-2-thienyl)-methylene]-2,4(3H,5H)-furandione

HRID 982404

反応式

HRID 982404 の反応式
[CH2:1]1[C:6](=[O:7])[O:5][CH2:4][C:2]1=[O:3].C([C:10]1[CH:14]=[C:13]([C:15]([OH:17])=[O:16])[S:12][C:11]=1[CH:18]=O)C.[CH2:20]1COC[CH2:21]1>>[CH2:20]([O:17][C:15]([C:13]1[S:12][C:11]([CH:18]=[C:1]2[C:2](=[O:3])[CH2:4][O:5][C:6]2=[O:7])=[CH:10][CH:14]=1)=[O:16])[CH3:21]

参加物

4

反応物 3

HCID 8028TetrahydrofuranHCID 521261Tetronic acidHCID 200677334-Ethyl-5-formyl-thiophene-2-carboxylic acid

生成物 1

HCID 538066413-[(5-ethoxycarbonyl-2-thienyl)-methylene]-2,4(3H,5H)-furandione収率 63%

実験手順

0.494 gm of tetronic acid (FW=100, 4.94 mmole) and 2.00 gm of ethyl-5-carboxy-2-thiophenecarboxaldehyde (FW=184, 10.9 mole) in 2mL of THF and 10 mL of concentrated HC1 was reacted as before by applying heat and efficient stirring. The total reaction time was 10 minutes. Workup and recrystallization from methanol gave 0.827 gm (63%) of the product. M. p. 204°-205.5° C. C12H10O4S: %C 564.13; %H 3.79; found %C 53.93; %H 4.00. NMR results: 1HNMR (d6DMSO (H2)/TMS δ1.39 (3H, t, 7HZ); 4.39 (2H, q, 7Hz); 7.83 (1H, d, 4Hz); 8.21 (2H, m).

後処理

  1. temperatureby applying heat
  2. customWorkup and recrystallization from methanol

出典と根拠

ORDレコード
ord-90d536ed0ea7481fb3e808f3653f70c9
出典データセット
uspto-grants-1991_02
特許番号
US04996227

関連ノート

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