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

HRID 982404

반응식

HRID 982404 반응식
[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]

참가 물질

4

반응물 3

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

생성물 1

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

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-90d536ed0ea7481fb3e808f3653f70c9
출처 데이터셋
uspto-grants-1991_02
특허 번호
US04996227

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