Ethyl 2-ethylnicotinate → (2-Ethylpyridin-3-yl)methanol

HRID 1035024노트

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HRID 1035024 반응식
[H-].[H-].[H-].[H-].[Li+].[Al+3].C([O:9][C:10](=O)[C:11]1[CH:16]=[CH:15][CH:14]=[N:13][C:12]=1[CH2:17][CH3:18])C>O1CCCC1>[CH2:17]([C:12]1[C:11]([CH2:10][OH:9])=[CH:16][CH:15]=[CH:14][N:13]=1)[CH3:18]

참가 물질

4

반응물 2

HCID 14580149Ethyl 2-ethylnicotinateHCID 21226445Aluminium lithium hydride

생성물 1

HCID 19690951(2-Ethylpyridin-3-yl)methanol수율 69.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

To a suspension of LiAlH4 (0.83 g, 21.76 mmol) in tetrahydrofuran (50 ml) was added drop wise a solution of 2-ethyl-nicotinic acid ethyl ester (Breitmaier et al, Tetrahedron, 26, 1970, 5907-5910) (3 g, 16.74 mmol) in tetrahydrofuran (25 ml) at −50° C. After addition, the temperature was slowly allowed to increase to 0° C. After 3 h, the reaction was quenched with saturated NH4Cl, filtered and washed with 1M NaHCO3 (50 ml). The aqueous layer was extracted with ethyl acetate (3×50 ml). Combined organic extract were dried (Na2SO4), filtered and concentrated to yield 1.6 g (54%) of product as a yellowish liquid. MS (ESI+) m/z 138 (M+H)+;

후처리

  1. additionAfter addition
  2. customthe reaction was quenched with saturated NH4Cl
  3. filtrationfiltered
  4. washwashed with 1M NaHCO3 (50 ml)
  5. extractionThe aqueous layer was extracted with ethyl acetate (3×50 ml)
  6. extractionCombined organic extract
  7. dry with materialwere dried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-ca5c0785d1844c4cae37f053a7064c94
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546374B2

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