Water → HCID 22612380、化合物

HRID 844012ノート

反応式

HRID 844012 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([C:8](O)=[O:9])[S:5][C:6]=1[Cl:7].S(Cl)(Cl)=O.[BH4-].[Na+].O>C(Cl)Cl.O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][OH:9])[S:5][C:6]=1[Cl:7]

参加物

7

反応物 4

HCID 962Water2 回HCID 24386Thionyl ChlorideHCID 3056874,5-Dichlorothiophene-2-carboxylic acidHCID 4311764Sodium borohydride

生成物 1

HCID 22612380HCID 22612380、化合物収率 144.9%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
0 °C

実験手順

To a solution of 4,5-Dichloro-thiophene-2-carboxylic acid (0.500 grams, 2.53 mmole) and thionyl chloride (1.0 ml) in methylene chloride (10 ml) was refluxed for 3 hours. The mixture was concentrated to remove solvent and diluted with 15 ml dioxane and sodium borohydride (0.143 grams, 3.8 mmole) and refluxed for 3 hours. The mixture was cooled to 0° C. and 3 ml water was added dropwise. The mixture was poured into 100 ml water. This was extracted with diethyl ether, washed with 1N NaOH, water, and brine, dried over MgSO4, filtered and concentrated to an oil which was purified via flash chromatography on silica using 30% ethyl acetate/hexane as eluent to give an oil (0.671 g). MW 183.06; MS (m/e) 184 (M++1).

後処理

  1. concentrationThe mixture was concentrated
  2. customto remove solvent
  3. temperaturerefluxed for 3 hours
  4. extractionThis was extracted with diethyl ether
  5. washwashed with 1N NaOH, water, and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated to an oil which
  9. customwas purified via flash chromatography on silica using 30% ethyl acetate/hexane as eluent

出典と根拠

ORDレコード
ord-45eeefc3df914708874fe93ba07a9b04
出典データセット
uspto-grants-2002_04
特許番号
US06380218B1

反応ノート

読み込み中…