Sodium Iodide → Trans-2-(Cyanomethyl)-5-(2'-methoxy-5'-fluorophenethyl)tetrahydrofuran

HRID 1919517ノート

反応式

HRID 1919517 の反応式
Br[CH2:2][CH:3]1[CH2:7][CH2:6][CH:5]([CH2:8][CH2:9][C:10]2[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=2[O:17][CH3:18])[O:4]1.[Na+].[I-].[C-:21]#[N:22].[K+].[Na].C([O-])(O)=O.[Na+]>O.CS(C)=O>[C:21]([CH2:2][C@H:3]1[CH2:7][CH2:6][C@H:5]([CH2:8][CH2:9][C:10]2[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=2[O:17][CH3:18])[O:4]1)#[N:22]

参加物

8

反応物 5

HCID 5238Sodium IodideHCID 9032Potassium CyanideHCID 516892Sodium BicarbonateHCID 5360545SodiumHCID 674993232-(Bromomethyl)-5-(2'-methoxy-5'-fluorophenethyl)tetrahydrofuran

生成物 1

HCID 86623855Trans-2-(Cyanomethyl)-5-(2'-methoxy-5'-fluorophenethyl)tetrahydrofuran収率 86%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

反応条件

温度
70 °C

実験手順

To a vial under Ar(g) was added 2-(bromomethyl)-5-(2′-methoxy-5′-fluorophenethyl)tetrahydrofuran (0.67 g, 2.1 mmol), NaI (70 mg), potassium cyanide (0.35 g, 5.3 mmol), and dry DMSO (5 mL). The mixture thus obtained was heated to 70° C. under Ar for 12 h. After it was cooled to room temperature, the reaction mixture was poured into a separatory funnel containing sodium bicarcarbonate aqueous solution (sat. NaHCO3:H2O=1:1, 40 mL). The organic function was extracted with ethyl acetate (2×50 mL) and the combined organic layers were washed with brine (50 mL) and dried over sodium sulfate. The solvent then was removed in vacuo and crude product thus obtained was purified by flash column chromatography (15% EtOAc in hexane) to result in the title product (448 mg, 86%).

後処理

  1. customThe mixture thus obtained
  2. temperatureAfter it was cooled to room temperature
  3. additionthe reaction mixture was poured into a separatory funnel
  4. extractionThe organic function was extracted with ethyl acetate (2×50 mL)
  5. washthe combined organic layers were washed with brine (50 mL)
  6. dry with materialdried over sodium sulfate
  7. customThe solvent then was removed in vacuo and crude product
  8. customthus obtained
  9. customwas purified by flash column chromatography (15% EtOAc in hexane)

出典と根拠

ORDレコード
ord-d7b364658c144320a428647d402c70d9
出典データセット
uspto-grants-2012_05
特許番号
US08168635B2

反応ノート

読み込み中…