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

HRID 2375562노트

반응식

HRID 2375562 반응식
[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

참가 물질

4

반응물 3

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

생성물 1

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

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-2c40f2d070c64193a208144e751dfb42
출처 데이터셋
uspto-grants-2008_12
특허 번호
US07465798B2

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