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

HRID 10225ノート

反応式

HRID 10225 の反応式
[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

参加物

3

反応物 1

HCID 521033(2-Thienylthio)acetone

生成物 1

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

試薬・触媒・溶媒 1

HCID 7964Chlorobenzene溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-55636809cd184363ae45824e305f8195
出典データセット
uspto-grants-2006_08
特許番号
US07094777B2

反応ノート

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