Water → 2-(4,5-Dichloro-thiophen-2-ylmethyl)-isoindole-1,3-dione

HRID 844011ノート

反応式

HRID 844011 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8]O)[S:5][C:6]=1[Cl:7].[C:10]1(=[O:20])[NH:14][C:13](=[O:15])[C:12]2=[CH:16][CH:17]=[CH:18][CH:19]=[C:11]12.N(C(OCC)=O)=NC(OCC)=O.O>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][N:14]2[C:10](=[O:20])[C:11]3[C:12](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:13]2=[O:15])[S:5][C:6]=1[Cl:7]

参加物

6

反応物 4

HCID 962WaterHCID 6809PhthalimideHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 22612380HCID 22612380、化合物

生成物 1

HCID 226120382-(4,5-Dichloro-thiophen-2-ylmethyl)-isoindole-1,3-dione収率 68.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of (4,5-Dichloro-thiophen-2-yl)-methanol (0.660 grams, 3.60 mmole), Phthalimide (0.636 grams, 4.32 mmole), and triphenyl phosphene (1.1 grams, 4.32 mmole) in tetrahydrofuran (20 ml) at room temperature was added diethyl azodicarboxylate (0.395 grams, 12.3 mmole) and stirred at room temperature over night. The mixture was poured into 100 ml water and extracted with diethyl ether. The combined extracts were washed with 1 N NaOH, water and brine, dried over MgSO4, filtered, and concentrated to an oil from which triphenylphosphine was crystalized out using diethyl ether/hexane. The mother liquor was concentrated to give a solid which was purified via flash chromatography on silica using 30% ethyl acetate/hexane as eluent to give a yellow solid. This was triturated in hexane to give a white solid (0.772 g). MW 312.18; MS (m/e) 313 (M++1).

後処理

  1. extractionextracted with diethyl ether
  2. washThe combined extracts were washed with 1 N NaOH, water and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to an oil from which triphenylphosphine
  6. customwas crystalized out
  7. concentrationThe mother liquor was concentrated
  8. customto give a solid which
  9. customwas purified via flash chromatography on silica using 30% ethyl acetate/hexane as eluent
  10. customto give a yellow solid
  11. customThis was triturated in hexane

出典と根拠

ORDレコード
ord-00b6f0555b8c46d3b56778caa0e921b9
出典データセット
uspto-grants-2002_04
特許番号
US06380218B1

反応ノート

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