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Water → Ethyl 3-cyclopropyl-3-(6-methoxypyrimidin-4-yl)acrylate

HRID 709608
ノート
印刷プレビュー

反応式

HRID 709608 の反応式
[H-].[Na+].C(OP([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])(OCC)=O)C.[CH:17]1([C:20]([C:22]2[CH:27]=[C:26]([O:28][CH3:29])[N:25]=[CH:24][N:23]=2)=O)[CH2:19][CH2:18]1.O>C1COCC1>[CH:17]1([C:20]([C:22]2[CH:27]=[C:26]([O:28][CH3:29])[N:25]=[CH:24][N:23]=2)=[CH:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:18][CH2:19]1
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

6

反応物 4

HCID 962WaterHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 91618935Cyclopropyl(6-methoxypyrimidin-4-yl)methanone

生成物 1

HCID 131733897Ethyl 3-cyclopropyl-3-(6-methoxypyrimidin-4-yl)acrylate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

Under a nitrogen atmosphere, to a suspension of 60% sodium hydride (2.13 g) in THF (100 ml) was added ethyl diethylphosphonoacetate (13.2 mL) at 0° C. To the obtained solution was added cyclopropyl(6-methoxypyrimidin-4-yl)methanone (entire amount) obtained in Example 2, step C, and the mixture was stirred at 0° C. for 1 hr. Water was added to the reaction mixture at room temperature, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give an isomer mixture of the title compound (E:Z=93:7 or 7:93, 5.57 g) as a yellow oil.

後処理

  1. customobtained in Example 2, step C
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)
  7. customto give

出典と根拠

ORDレコード
ord-60e26fcb8d5646638e180e7781a4dc51
出典データセット
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09181186B2

反応ノート

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