3-Pyridinecarboxaldehyde → [4-(Tert-butyldimethylsilyloxymethyl)-phenyl]-pyridin-3-yl-methanol

HRID 911708

反応式

HRID 911708 の反応式
[Si:1]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13](Br)=[CH:12][CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Li]CCCC.[N:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH:28]=[O:29])[CH:23]=1>C1COCC1>[Si:1]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH:28]([C:24]2[CH:23]=[N:22][CH:27]=[CH:26][CH:25]=2)[OH:29])=[CH:12][CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

参加物

5

反応物 3

HCID 103713-PyridinecarboxaldehydeHCID 108595834-Bromobenzyloxy-tert-butyldimethylsilaneHCID 178418339Butyllithium

生成物 1

HCID 23302982[4-(Tert-butyldimethylsilyloxymethyl)-phenyl]-pyridin-3-yl-methanol収率 35%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

Dissolve 4-(tert-butyldimethylsilyloxymethyl)bromobenzene (1 g, 3.319 mmol, prepared by following the procedure described in J. Am. Chem. Soc. 1995, 117, 704-714) in anhydrous THF (20 mL). Cool the solution to −78° C., add n-BuLi (4.149 mL, 6.638 mmol, 1.6M solution in hexane) and stir at this temperature for 1.5 h. Warm to −60° C., stir for an additional 30 min and add 3-pyridine carboxaldehyde. Allow the reaction mixture to warm gradually to room temperature and stir overnight. Add brine and extract with EtOAc. Dry the organic phase over Na2SO4, filter and concentrate in vacuo. Purify the crude mixture by chromatography on silica gel eluting sequentially with hexane and EtOAc to give the desired intermediate (380 mg, 35%). MS (ES+) m/z: 330 (M+H)*.

後処理

  1. customprepared
  2. temperatureWarm to −60° C.
  3. stirringstir for an additional 30 min
  4. temperatureto warm gradually to room temperature
  5. stirringstir overnight
  6. extractionAdd brine and extract with EtOAc
  7. dry with materialDry the organic phase over Na2SO4
  8. filtrationfilter
  9. concentrationconcentrate in vacuo
  10. customPurify the crude mixture by chromatography on silica gel eluting sequentially with hexane and EtOAc

出典と根拠

ORDレコード
ord-072283dcc40a409990eb3aa9b8014da3
出典データセット
uspto-grants-2011_09
特許番号
US08022062B2

関連ノート

読み込み中…