Ethyl 7-(Formylamino)chroman-2-carboxylate → [7-(Methylamino)-3,4-dihydro-2H-chromen-2-yl]methanol

HRID 49465ノート

反応式

HRID 49465 の反応式
[CH:1]([NH:3][C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH:10]([C:14](OCC)=[O:15])[O:11]2)=[CH:6][CH:5]=1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH3:1][NH:3][C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH:10]([CH2:14][OH:15])[O:11]2)=[CH:6][CH:5]=1

参加物

4

反応物 2

HCID 20637412Ethyl 7-(Formylamino)chroman-2-carboxylateHCID 21226445Aluminium lithium hydride

生成物 1

HCID 11480975[7-(Methylamino)-3,4-dihydro-2H-chromen-2-yl]methanol収率 98%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of ethyl 7-(formylamino)chroman-2-carboxylate (1.54 g; 6.00 mmol) in anhydrous THF, under nitrogen, is treated dropwise with a 1 M solution of lithium aluminum hydride in THF (30 mL; 30 mmol), stirred at ambient temperature for 4 h, quenched with a 10% solution of water in THF, with cooling as necessary to maintain room temperature, poured into water and extracted with ethyl acetate. The combined extracts are washed with brine, dried over MgSO4 and concentrated in vacuo to afford the title compound as a straw colored oil (1.13 g; 98% yield), identified by NMR spectral analysis.

後処理

  1. customquenched with a 10% solution of water in THF
  2. temperaturewith cooling as necessary
  3. temperatureto maintain room temperature
  4. additionpoured into water
  5. extractionextracted with ethyl acetate
  6. washThe combined extracts are washed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-2edac40d02fd4847a204010bb8f8c0c6
出典データセット
uspto-grants-2004_03
特許番号
US06706757B2

反応ノート

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