Thionyl Chloride → 1-(Benzo[b]thiophen-3-yl)-3-chloropropan-2-one

HRID 2375562ノート

反応式

HRID 2375562 の反応式
[Cl:1][CH2:2]C(=O)CC1SC=CC=1.[S:11]1[CH:15]=[C:14]([CH2:16][C:17]([OH:19])=O)[C:13]2[CH:20]=[CH:21][CH:22]=[CH:23][C:12]1=2.S(Cl)(Cl)=O>>[S:11]1[CH:15]=[C:14]([CH2:16][C:17](=[O:19])[CH2:2][Cl:1])[C:13]2[CH:20]=[CH:21][CH:22]=[CH:23][C:12]1=2

参加物

4

反応物 3

HCID 24386Thionyl ChlorideHCID 70799Benzo[b]thiophene-3-acetic acidHCID 161002061-Chloro-3-(thiophen-2-yl)propan-2-one

生成物 1

HCID 161001791-(Benzo[b]thiophen-3-yl)-3-chloropropan-2-one収率 56%

実験手順

The procedure described above for the synthesis of 1-chloro-3-(thiophen-2-yl)propan-2-one was followed. To prepare the acid chloride, 2-(benzo[b]thiophen-3-yl)acetic acid (1.00 g, 5.20 mmol) was added to 6 mL thionyl chloride in a 25 mL round-bottomed flask. The mixture was stirred overnight at room temperature, and the thionyl chloride then removed in vacuo and the residue azeotroped twice with toluene. The acid chloride was then reacted with diazomethane and HCl. The crude product was purified by flash chromatography over silica gel (2-30% ethyl acetate in hexanes) to give pure material (0.661 g, 56% yield): 1H NMR (400 MHz, CDCl3) δ 4.12 (s, 2H) 4.14 (d, J=1.0 Hz, 2H) 7.36-7.44 (m, 3H) 7.67-7.71 (m, 1H) 7.87-7.90 (m, 1H).

後処理

  1. customthe thionyl chloride then removed in vacuo
  2. customthe residue azeotroped twice with toluene
  3. customThe acid chloride was then reacted with diazomethane and HCl
  4. customThe crude product was purified by flash chromatography over silica gel (2-30% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-2c40f2d070c64193a208144e751dfb42
出典データセット
uspto-grants-2008_12
特許番号
US07465798B2

反応ノート

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