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Diethyl (cyanomethyl)phosphonate → 3-[3-(5-Ethyl-2,6-dimethoxy-pyrimidine-4-carbonyl)-5-methyl-phenyl]-acrylonitrile

HRID 426187
ノート
印刷プレビュー

反応式

HRID 426187 の反応式
[CH2:1]([C:3]1[C:4]([C:13]([C:15]2[CH:16]=[C:17]([CH:20]=[C:21]([CH3:23])[CH:22]=2)[CH:18]=O)=[O:14])=[N:5][C:6]([O:11][CH3:12])=[N:7][C:8]=1[O:9][CH3:10])[CH3:2].[C:24]([CH2:26]P(=O)(OCC)OCC)#[N:25].CC(C)([O-])C.[K+]>C1COCC1>[CH2:1]([C:3]1[C:4]([C:13]([C:15]2[CH:16]=[C:17]([CH:18]=[CH:26][C:24]#[N:25])[CH:20]=[C:21]([CH3:23])[CH:22]=2)=[O:14])=[N:5][C:6]([O:11][CH3:12])=[N:7][C:8]=1[O:9][CH3:10])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 75676Diethyl (cyanomethyl)phosphonateHCID 23665647Potassium tert-butoxideHCID 591848303-(5-Ethyl-2,6-dimethoxy-pyrimidine-4-carbonyl)-5-methyl-benzaldehyde

生成物 1

HCID 667055223-[3-(5-Ethyl-2,6-dimethoxy-pyrimidine-4-carbonyl)-5-methyl-phenyl]-acrylonitrile収率 72%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred mixture of 3-(5-ethyl-2,6-dimethoxy-pyrimidine-4-carbonyl)-5-methyl-benzaldehyde (3.11 g, 9.9 mmol) and diethyl cyanomethyl-phosphonate (1.6 ml, 10 mmol) in anhydrous THF (20 ml) at 0° C. (ice bath) under nitrogen atmosphere, was added potassium t-butoxide (1.26 g, 11.2 mmol). After 1 hr., the mixture was stirred at room temperature for 5 hr. The mixture was then partitioned between ether and water. The ether layer was taken, dried with anhydrous magnesium sulfate, filtered, and evaporated in vacuo to give a pale yellow syrup. The crude product was purified by silica gel column chromatography (eluent, EA:hexanes (1:4)) to afford 2.39 g (72%) of a white solid. m.p. 165-166° C.; 1H NMR (200 MHz, CDCl3) δ 1.09 (3H, t, J=7.8 Hz), 2.42-2.53 (5H, m), 3.96 (3H, s), 4.09 (3H, s), 5.93 (1H, d, J=16.8 Hz), 7.40 (1H, s, J=16.8 Hz), 7.50 (1H, s), 7.73 (1H, s), 7.79 (1H, s).

後処理

  1. customThe mixture was then partitioned between ether and water
  2. dry with materialdried with anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customto give a pale yellow syrup
  6. customThe crude product was purified by silica gel column chromatography (eluent, EA:hexanes (1:4))

出典と根拠

ORDレコード
ord-9371bccb9ea64dc383f4d0fbce7f8271
出典データセット
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08106064B2

反応ノート

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