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

HRID 49465노트

반응식

HRID 49465 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-2edac40d02fd4847a204010bb8f8c0c6
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06706757B2

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