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

HRID 1035024ノート

反応式

HRID 1035024 の反応式
[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]

参加物

4

反応物 2

HCID 14580149Ethyl 2-ethylnicotinateHCID 21226445Aluminium lithium hydride

生成物 1

HCID 19690951(2-Ethylpyridin-3-yl)methanol収率 69.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

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)+;

後処理

  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

出典と根拠

ORDレコード
ord-ca5c0785d1844c4cae37f053a7064c94
出典データセット
uspto-grants-2013_10
特許番号
US08546374B2

反応ノート

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