Dimethylformamide → 5-Fluoro-2,3-dihydro-1,4-benzodioxin-6-carbaldehyde

HRID 1943238ノート

反応式

HRID 1943238 の反応式
Br[C:2]1[CH:11]=[CH:10][C:5]2[O:6][CH2:7][CH2:8][O:9][C:4]=2[C:3]=1[F:12].[Li]CCCC.CN([CH:21]=[O:22])C>C1COCC1>[F:12][C:3]1[C:4]2[O:9][CH2:8][CH2:7][O:6][C:5]=2[CH:10]=[CH:11][C:2]=1[CH:21]=[O:22]

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 124645241,4-Benzodioxin, 6-bromo-5-fluoro-2,3-dihydro-HCID 178418339Butyllithium

生成物 1

HCID 866421125-Fluoro-2,3-dihydro-1,4-benzodioxin-6-carbaldehyde収率 22%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

A solution of 6-bromo-5-fluoro-2,3-dihydro-1,4-benzodioxin (146 mg, 0.627 mmol) in THF (5 ml) at −78° C. was treated with n-BuLi (0.551 ml, 1.378 mmol) under a nitrogen atmosphere and stirred at −78° C. for 15 min before treatment with a solution of DMF (0.243 ml, 3.13 mmol) in THF) (2.00 ml). The reaction was stirred for 10 min at −78° C. and then the reaction was allowed warm to rt over 10 min and stirred at rt for 0.5 h. Reaction was treated with 2M HCl (20 ml) and extracted with ethyl acetate (3×100 ml). The organic extracts were evaporated, dried (MgSO4), filtered, evaporated, chromatographed (0-100% EtOAC:Cyclohexane) to give product as a white solid (25 mg, 22%).

後処理

  1. temperaturethe reaction was allowed warm to rt over 10 min
  2. stirringstirred at rt for 0.5 h
  3. customReaction
  4. extractionextracted with ethyl acetate (3×100 ml)
  5. customThe organic extracts were evaporated
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated
  9. customchromatographed (0-100% EtOAC:Cyclohexane)

出典と根拠

ORDレコード
ord-6c56a9e2edb34fceaa0c6566e8b08525
出典データセット
uspto-grants-2013_03
特許番号
US08389524B2

反応ノート

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