Sodium Hydroxide → HCID 124399918、化合物

HRID 1807404ノート

反応式

HRID 1807404 の反応式
[I-].[CH3:2][S+](C)(C)=O.[OH-].[Na+].[Cl:9][C:10]1[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=1/[CH:17]=[CH:18]/[C:19](=[O:21])[CH3:20]>CS(C)=O>[Cl:9][C:10]1[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=1[C@@H:17]1[CH2:2][C@H:18]1[C:19](=[O:21])[CH3:20]

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 5849647HCID 5849647、化合物

生成物 1

HCID 124399918HCID 124399918、化合物

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒2 回

実験手順

A round bottom flask equipped with magnetic stirrer, nitrogen inlet and additional funnel was charged with trimethylsulfoxonium iodide (0.61 g, 2.78 mmol), DMSO (10 ml) and powdered sodium hydroxide (97 mg, 2.44 mmol). The suspension was stirred for 1.0 hour at ambient temperature to yield a solution. So prepared solution was added drop wise at ambient temperature to a solution of (E)-4-(2,4-dichloro-phenyl)-but-3-en-2-one (0.50 g, 2.32 mmol) prepared as described in example P30 in DMSO (10 ml). The reaction mixture was stirred for 0.5 hours, poured onto ice water (100 ml) and extracted with ether (3×25 ml). Combined organic layers were washed with water, brine and dried over anhydrous sodium sulfate. The solvent was removed in vacuo and the residue was purified by flash chromatography over silica gel (25 g) (eluent: n-hexane/ethyl acetate 10:1) to afford 0.33 g (62% of theory) of trans 1-[2-(2,4-dichloro-phenyl)-cyclopropyl]-ethyanone in form of an oil.

後処理

  1. customA round bottom flask equipped with magnetic stirrer, nitrogen inlet and additional funnel
  2. customto yield a solution
  3. customSo prepared solution
  4. customprepared
  5. stirringThe reaction mixture was stirred for 0.5 hours
  6. additionpoured onto ice water (100 ml)
  7. extractionextracted with ether (3×25 ml)
  8. washCombined organic layers were washed with water, brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. customThe solvent was removed in vacuo
  11. customthe residue was purified by flash chromatography over silica gel (25 g) (eluent: n-hexane/ethyl acetate 10:1)
  12. customto afford 0.33 g (62% of theory) of trans 1-[2-(2,4-dichloro-phenyl)-cyclopropyl]-ethyanone in form of an oil

出典と根拠

ORDレコード
ord-2d98c99f9f5c409eacffb117f2ee8412
出典データセット
uspto-grants-2013_01
特許番号
US08357635B2

反応ノート

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