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

HRID 32069

반응식

HRID 32069 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-91a8661e4ce5415794b20c22b66ec1ea
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07425631B2

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