Water → 6-(2,4-Difluorophenoxy)-2-formylnicotinonitrile

HRID 1620408ノート

反応式

HRID 1620408 の反応式
[F:1][C:2]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:3]=1[O:4][C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[C:7](/[CH:13]=C/N(C)C)[N:6]=1.O.I([O-])(=O)(=O)=[O:25].[Na+]>C1COCC1>[F:1][C:2]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:3]=1[O:4][C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[C:7]([CH:13]=[O:25])[N:6]=1

参加物

5

反応物 3

HCID 962WaterHCID 23667635Sodium periodateHCID 86664562(E)-6-(2,4-Difluorophenoxy)-2-(2-(dimethylamino)vinyl)nicotinonitrile

生成物 1

HCID 848198116-(2,4-Difluorophenoxy)-2-formylnicotinonitrile

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

At RT, to the product of step 2 above in THF (70.00 mL) and water (70.00 mL) was added sodium periodate (8.9 g, 42 mmol) in one portion and the reaction mixture was allowed to stir at RT for 2 h, resulting in the formation of a yellow suspension. The suspension was passed through a flitted funnel, washing with THF (2×10 mL). The filtrate was concentrated under reduced pressure and the remaining mixture was extracted with DCM (2×30 mL). The organic layers were combined, dried over MgSO4, filtered and concentrated. Purification on the ISCO (40 g column, 20-60% EtOAc in hexanes) afforded 6-(2,4-difluorophenoxy)-2-formylnicotinonitrile as a light yellow crystalline solid. MS (ESI, pos.ion) m/z: M+1=261.0

後処理

  1. customresulting in the formation of a yellow suspension
  2. customThe suspension was passed through a flitted funnel
  3. washwashing with THF (2×10 mL)
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. extractionthe remaining mixture was extracted with DCM (2×30 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification on the ISCO (40 g column, 20-60% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-89bca07b03de484bbddf0e28ee5344bf
出典データセット
uspto-grants-2014_07
特許番号
US08772481B2

反応ノート

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