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Water → [4-(4-Fluorophenyl)-5-(methoxymethyl)-2,6-di(propan-2-yl)pyridin-3-yl]methanol

HRID 1681254
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HRID 1681254 반응식
[CH:1]([C:4]1[C:9]([C:10](OCC)=[O:11])=[C:8]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[C:7]([CH2:22][O:23][CH3:24])=[C:6]([CH:25]([CH3:27])[CH3:26])[N:5]=1)([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[K+]>O1CCCC1>[CH:1]([C:4]1[C:9]([CH2:10][OH:11])=[C:8]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[C:7]([CH2:22][O:23][CH3:24])=[C:6]([CH:25]([CH3:27])[CH3:26])[N:5]=1)([CH3:3])[CH3:2]
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HCID 962WaterHCID 14797Potassium HydroxideHCID 18926957Ethyl 2,6-diisopropyl-4-(4-fluorophenyl)-5-methoxymethylpyridine-3-carboxylateHCID 21226445Aluminium lithium hydride

생성물 1

HCID 18926938[4-(4-Fluorophenyl)-5-(methoxymethyl)-2,6-di(propan-2-yl)pyridin-3-yl]methanol

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매
2회

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온도
0 °C

실험 절차

2.85 g (7.6 mmol) of the compound from Example 59 dissolved in 30 ml of absolute tetrahydrofuran are added dropwise under a nitrogen atmosphere to 0.5 g (13.2 mmol) of lithium aluminum hydride in 20 ml of absolute tetrahydrofuran at 60° C. The mixture is heated to reflux for 1 hour, subsequently cooled to 0° C. and 1.5 ml of water and 0.3 ml of 15% strength potassium hydroxide solution are cautiously added dropwise. The solution is filtered from the deposited precipitate with suction and the latter is boiled several times with ether. The combined phases are dried over magnesium sulphate and concentrated in vacuo. The residue is chromatographed on a column (silica gel 70-230 mesh, using ethyl acetate/petroleum ether 1:9).

후처리

  1. temperatureThe mixture is heated
  2. temperatureto reflux for 1 hour
  3. filtrationThe solution is filtered from the deposited precipitate with suction
  4. dry with materialThe combined phases are dried over magnesium sulphate
  5. concentrationconcentrated in vacuo
  6. customThe residue is chromatographed on a column (silica gel 70-230 mesh, using ethyl acetate/petroleum ether 1:9)

출처 및 근거

ORD 기록
ord-a33514f2a859402eab2fdc17e17f6619
출처 데이터셋
uspto-grants-1992_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05169857

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