Potassium Sodium Tartrate → 3,4-Dihydro-2H-1-benzopyran-4-amine

HRID 32069

反応式

HRID 32069 の反応式
[H-].[H-].[H-].[H-].[Li+].[Al+3].[O:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10](=[N:17]O)[CH2:9][CH2:8]1.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C1COCC1.O>[O:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]([NH2:17])[CH2:9][CH2:8]1

参加物

6

反応物 3

HCID 9357Potassium Sodium TartrateHCID 44866984H-1-Benzopyran-4-one, 2,3-dihydro-, oximeHCID 21226445Aluminium lithium hydride

生成物 1

HCID 49619573,4-Dihydro-2H-1-benzopyran-4-amine

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

LAH (6.35 g, 167 mmol) was suspended in THF (100 mL) at 0° C. A solution of chroman-4-one oxime (Step A) (10.92 g, 66.92 mmol) in THF (100 mL) was added drop-wise. The mixture was heated slowly to reflux for 4 h. The reaction was cooled to RT and added drop-wise to a stirred saturated solution of Rochelle's salt in H2O. The bi-phasic mixture was stirred rapidly at RT for 1 h. The layers were separated and the aqueous layer was extracted with EtOAc until tlc analysis of the aqueous layer showed no evidence of the title compound. The combined organics were dried over MgSO4 and concentrated in vacuo to furnish the crude material, which was purified by flash column chromatography to afford the title compound. MS (APCI pos) 150 (M+H).

後処理

  1. temperatureThe mixture was heated slowly
  2. temperatureto reflux for 4 h
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with EtOAc until tlc analysis of the aqueous layer
  5. dry with materialThe combined organics were dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customto furnish the crude material, which
  8. customwas purified by flash column chromatography

出典と根拠

ORDレコード
ord-91a8661e4ce5415794b20c22b66ec1ea
出典データセット
uspto-grants-2008_09
特許番号
US07425631B2

関連ノート

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