Aluminium lithium hydride → (3,5-Diethylpyridin-4-yl)methanol

HRID 577107노트

반응식

HRID 577107 반응식
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([C:9]1[CH:10]=[N:11][CH:12]=[C:13]([CH2:20][CH3:21])[C:14]=1[C:15](OCC)=[O:16])[CH3:8]>C1COCC1>[CH2:20]([C:13]1[CH:12]=[N:11][CH:10]=[C:9]([CH2:7][CH3:8])[C:14]=1[CH2:15][OH:16])[CH3:21]

참가 물질

4

반응물 2

HCID 21226445Aluminium lithium hydrideHCID 59589455Ethyl 3,5-diethylpyridine-4-carboxylate

생성물 1

HCID 59589408(3,5-Diethylpyridin-4-yl)methanol수율 86%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a suspension of LAH (0.805 g, 21.22 mmol) in anhydrous THF (20 mL) at 0° C. was added a dropwise a solution of ethyl 3,5-diethylpyridine-4-carboxylate (2.20 g, 10.61 mmol) in THF (30 mL). After stirring for 1 hour, the reaction mixture was slowly quenched with 15% NaOH solution and then diluted with water. Ethyl acetate was added, the mixture was stirred for 10 minutes, and the precipitated white solid was filtered off. The solid was washed with ethyl acetate (2×50 mL). The combined organic layers were dried over anhydrous sodium sulfate and filtered. The filtrate was evaporated to provide (3,5-diethylpyridin-4-yl)methanol as a thick oil (1.50 g, 86% yield) which was used for the next step without any further purification; 1H NMR (400 MHz, DMSO-d6): δ 1.15 (t, 6H), 2.70 (q, 4H), 4.50 (s, 2H), 5.06 (bs, 1H), 8.22 (s, 2H), M+ 208.5; M+ 166.2.

후처리

  1. customthe reaction mixture was slowly quenched with 15% NaOH solution
  2. additiondiluted with water
  3. additionEthyl acetate was added
  4. stirringthe mixture was stirred for 10 minutes
  5. filtrationthe precipitated white solid was filtered off
  6. washThe solid was washed with ethyl acetate (2×50 mL)
  7. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customThe filtrate was evaporated

출처 및 근거

ORD 기록
ord-549f6e03803a4704a593e2137ca58a9d
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040538B2

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