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

HRID 1919517노트

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HRID 1919517 반응식
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]

참가 물질

8

반응물 5

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

생성물 1

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

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

반응 조건

온도
70 °C

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-d7b364658c144320a428647d402c70d9
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08168635B2

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