(2-Thienylthio)acetone → Thieno(2,3-b)thiophene, 3-methyl-

HRID 10225노트

반응식

HRID 10225 반응식
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[S:6][CH2:7][C:8]([CH3:10])=O>ClC1C=CC=CC=1>[CH3:10][C:8]1[C:3]2[CH:4]=[CH:5][S:1][C:2]=2[S:6][CH:7]=1

참가 물질

3

반응물 1

HCID 521033(2-Thienylthio)acetone

생성물 1

HCID 137172Thieno(2,3-b)thiophene, 3-methyl-수율 42%

시약·촉매·용매 1

HCID 7964Chlorobenzene용매

실험 절차

A 1M solution of 1-(2-thienylthio)acetone (2.6 g, 15.1 mmol) in chlorobenzene (15 mL) was heated to 110° C. under nitrogen and hot polyphosphoric acid (3 mL) was added. The reaction was heated to reflux overnight. The chlorobenzene layer was decanted off and further chlorobenzene (15 mL x2) was added to the polyphosphoric acid residue and stirred at reflux for 30 minutes. The combined chlorobenzene extracts were concentrated in vacuo and purified by flash column chromatography on silica, eluting with 40% dichloromethane/isohexane, to give 3-methylthieno[2,3-b]thiophene (0.97 g, 42%). 1H NMR (500 MHz, CDCl3) δ 7.34 (1H, dd, J=1.0, 5.2 Hz), 7.16 (1H, d, J=5.2 Hz), 6.94 (1H, t, J=1.1 Hz), 2.40 (3H, d, J=1.1 Hz).

후처리

  1. temperatureThe reaction was heated
  2. temperatureto reflux overnight
  3. customThe chlorobenzene layer was decanted off
  4. additionfurther chlorobenzene (15 mL x2) was added to the polyphosphoric acid residue
  5. temperatureat reflux for 30 minutes
  6. concentrationThe combined chlorobenzene extracts were concentrated in vacuo
  7. custompurified by flash column chromatography on silica
  8. washeluting with 40% dichloromethane/isohexane

출처 및 근거

ORD 기록
ord-55636809cd184363ae45824e305f8195
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094777B2

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