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Cesium carbonate → (2E)-3-(4-tert-Butylphenyl)-3-(5-chloro-6-methoxypyridin-2-yl)prop-2-en-1-ol

HRID 70526
ノート
印刷プレビュー

反応式

HRID 70526 の反応式
[C:1]([C:5]1[CH:10]=[CH:9][C:8](B(O)O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].[Cl:36][C:37]1[CH:38]=[CH:39][C:40](/[C:45](/I)=[CH:46]/[CH2:47][OH:48])=[N:41][C:42]=1[O:43][CH3:44]>O1CCOCC1.C(OCC)(=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O>[C:1]([C:5]1[CH:10]=[CH:9][C:8](/[C:45](/[C:40]2[CH:39]=[CH:38][C:37]([Cl:36])=[C:42]([O:43][CH3:44])[N:41]=2)=[CH:46]\[CH2:47][OH:48])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

9

反応物 4

HCID 10796Cesium carbonateHCID 521585Tris(furan-2-yl)phosphaneHCID 27343204-tert-Butylphenylboronic acidHCID 58452855(2Z)-3-(5-Chloro-6-methoxypyridin-2-yl)-3-iodoprop-2-en-1-ol

生成物 1

HCID 58452849(2E)-3-(4-tert-Butylphenyl)-3-(5-chloro-6-methoxypyridin-2-yl)prop-2-en-1-ol収率 101.6%

試薬・触媒・溶媒 4

HCID 9811564
Bis(dibenzylideneacetone)palladium
触媒
HCID 962Water溶媒
HCID 8857Ethyl Acetate溶媒
HCID 312751,4-Dioxane溶媒

反応条件

温度
65 °C

実験手順

4-tert-Butylphenylboronic acid (3.5 g), tris(dibenzylideneacetone)dipalladium(0) (183 mg), tri(2-furyl)phosphine (280 mg) and cesium carbonate (1.98 g) were added to a solution of (2Z)-3-(5-chloro-6-methoxypyridin-2-yl)-3-iodoprop-2-en-1-ol (881 mg) in 1,4-dioxane (20 mL)-water (10 mL) in a nitrogen atmosphere, and the mixture was stirred at an external temperature of 65° C. for 1.5 hours. The reaction solution was left to cool, diluted with ethyl acetate and filtered. The filtrate was washed with brine and dried over sodium sulfate. After filtration, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=19:1→1:1) to give the title compound as a light yellow powder (912 mg, 91%).

後処理

  1. waitThe reaction solution was left
  2. temperatureto cool
  3. filtrationfiltered
  4. washThe filtrate was washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationAfter filtration
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=19:1→1:1)

出典と根拠

ORDレコード
ord-08a57a96d9184121a1cb0aadff6dac11
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08822503B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート