Water → HCID 22612380, 화합물

HRID 844012노트

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HRID 844012 반응식
[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]

참가 물질

7

반응물 4

HCID 962Water2회HCID 24386Thionyl ChlorideHCID 3056874,5-Dichlorothiophene-2-carboxylic acidHCID 4311764Sodium borohydride

생성물 1

HCID 22612380HCID 22612380, 화합물수율 144.9%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 312751,4-Dioxane용매

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온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-45eeefc3df914708874fe93ba07a9b04
출처 데이터셋
uspto-grants-2002_04
특허 번호
US06380218B1

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