Acetic Acid → 2-Cyano-3-(5-iodo-4-methyl-thiophen-2-yl)-but-2-enoic acid ethyl ester

HRID 1244145

반응식

HRID 1244145 반응식
C(O)(=O)C.C[Si](N[Si](C)(C)C)(C)C.[I:14][C:15]1[S:19][C:18]([C:20](=O)[CH3:21])=[CH:17][C:16]=1[CH3:23].[C:24]([CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])#[N:25]>CCOC(C)=O>[CH2:30]([O:29][C:27](=[O:28])[C:26]([C:24]#[N:25])=[C:20]([C:18]1[S:19][C:15]([I:14])=[C:16]([CH3:23])[CH:17]=1)[CH3:21])[CH3:31]

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 7764Ethyl cyanoacetateHCID 13838HexamethyldisilazaneHCID 219315451-(5-Iodo-4-methyl-thiophen-2-yl)-ethanone

생성물 1

HCID 696073602-Cyano-3-(5-iodo-4-methyl-thiophen-2-yl)-but-2-enoic acid ethyl ester수율 58.5%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
80 °C

실험 절차

Acetic acid (9.4 ml) was placed in a flask at rt and HMDS (3.0 ml, 14.1 mmol) was added dropwise. After the exotherm subsided, 1-(5-Iodo-4-methyl-thiophen-2-yl)-ethanone (2.5 g, 9.4 mmol) was added as a solid followed by ethyl cyanoacetate (2.0 ml, 18.8 mmol). The reaction was stirred at 80° C. for 8 h, cooled to rt and concentrated by rotary evaporation to give a brown residue. The residue was taken up in EtOAc, washed with NaHCO3 (aq, sat.) and then with H2O. The organics were dried (NaSO4), filtered and concentrated to give a brown solid. The solid was triturated with EtOH and filtered to give 2-Cyano-3-(5-iodo-4-methyl-thiophen-2-yl)-but-2-enoic acid ethyl ester (2.0 g, 5.5 mmol, 58%) as a light yellow solid. MS (ESI) m/z 362.0 (M+H+); 1H NMR (300 MHz, DMSO-d6) δ ppm 1.27 (t, 1H) 2.21 (s, 1H) 2.66 (s, 1H) 4.26 (q, 1H) 7.67 (s, 4H).

후처리

  1. temperaturecooled to rt
  2. concentrationconcentrated by rotary evaporation
  3. customto give a brown residue
  4. washwashed with NaHCO3 (aq, sat.)
  5. dry with materialThe organics were dried (NaSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a brown solid
  9. customThe solid was triturated with EtOH
  10. filtrationfiltered

출처 및 근거

ORD 기록
ord-37533cd780f941d3905b4fbf8deee233
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07119205B2

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