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Chlorosuccinimide → 2-Chloro-5-ethyl-thiophene-3-carboxylic acid ethyl ester

HRID 1809084
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HRID 1809084 반응식
[Cl:1]N1C(=O)CCC1=O.[CH2:9]([O:11][C:12]([C:14]1[CH:18]=[C:17]([CH2:19][CH3:20])[S:16][CH:15]=1)=[O:13])[CH3:10]>C(O)(=O)C>[CH2:9]([O:11][C:12]([C:14]1[CH:18]=[C:17]([CH2:19][CH3:20])[S:16][C:15]=1[Cl:1])=[O:13])[CH3:10]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 31398ChlorosuccinimideHCID 12588559Ethyl 5-ethylthiophene-3-carboxylate

생성물 1

HCID 595425792-Chloro-5-ethyl-thiophene-3-carboxylic acid ethyl ester수율 69.9%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

N-Chlorosuccinimide (0.8 g, 5.9 mmol) was added to a solution of 5-ethyl-thiophene-3-carboxylic acid ethyl ester (1 g, 5.43 mmol) in acetic acid (10 mL) and stirred overnight. The reaction was filtered and the solvent removed under vacuum. The product was purified by flash chromatography on silica, eluting with 0%-100% t-butylmethyl ether in cyclohexane. The fractions containing the desired product were concentrated under vacuum to give the title compound (0.83 g). 1H NMR (400 MHz, CHCl3-d): δ 7.05 (s, 1H), 4.3 (q, 2H), 2.75 (q, 2H), 1.4 (t, 3H), 1.3 (t, 3H).

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후처리

  1. filtrationThe reaction was filtered
  2. customthe solvent removed under vacuum
  3. customThe product was purified by flash chromatography on silica
  4. washeluting with 0%-100% t-butylmethyl ether in cyclohexane
  5. additionThe fractions containing the desired product
  6. concentrationwere concentrated under vacuum

출처 및 근거

ORD 기록
ord-0346fc020d8a4f0da45d3906449986b0
출처 데이터셋
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08362008B2

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