Hydrochloric Acid → 5-Fluoro-8-methoxychroman-6-carboaldehyde

HRID 1698691ノート

反応式

HRID 1698691 の反応式
[F:1][C:2]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][O:7]2.CN(CCN(CCN(C)C)C)C.C([Li])CCC.[CH:31](N1CCOCC1)=[O:32].Cl>C1COCC1>[F:1][C:2]1[C:11]([CH:31]=[O:32])=[CH:10][C:9]([O:12][CH3:13])=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][O:7]2

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 18196PentamethyldiethylenetriamineHCID 20417N-FormylmorpholineHCID 595118145-Fluoro-8-methoxychromaneHCID 178418339Butyllithium

生成物 1

HCID 595118625-Fluoro-8-methoxychroman-6-carboaldehyde

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-74 °C

実験手順

To a solution of 3.6 g of 5-fluoro-8-methoxychromane and 4.2 ml of N,N,N′,N′,N″-pentamethyldiethylenetriamine in 130 ml of THF there was added dropwise 8 ml of n-butyllithium (2.55 M, hexane solution) at −74° C. After stirring at −74° C. for 1 hour, N-formylmorpholine was added. After further stirring at room temperature for 1 hour, 1N hydrochloric acid was added to the reaction mixture while cooling on ice, and the mixture was extracted with ethyl acetate and dried over anhydrous magnesium sulfate. The desiccating agent was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-heptane) to give the title compound (1.50 g) as a white solid.

後処理

  1. stirringAfter further stirring at room temperature for 1 hour
  2. temperaturewhile cooling on ice
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe desiccating agent was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate-heptane)

出典と根拠

ORDレコード
ord-3771150a8d3d41e495a9d25f735dbfda
出典データセット
uspto-grants-2012_04
特許番号
US08163787B2

反応ノート

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