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Sodium hydride → 4-[(E)-2-cyanoethenyl]-1-[2-(trityloxy)ethyl]-5-aminopyrazole

HRID 349552
ノート
印刷プレビュー

反応式

HRID 349552 の反応式
[H-].[Na+].C(OP([CH2:11][C:12]#[N:13])(=O)OCC)C.[C:14]1([C:20]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[O:21][CH2:22][CH2:23][N:24]2[C:28]([NH2:29])=[C:27]([CH:30]=O)[CH:26]=[N:25]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>O1CCCC1>[C:12](/[CH:11]=[CH:30]/[C:27]1[CH:26]=[N:25][N:24]([CH2:23][CH2:22][O:21][C:20]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:28]=1[NH2:29])#[N:13]
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 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 179619611-(2-Triphenylmethyloxyethyl)-5-aminopyrazole-4-carbaldehyde

生成物 1

HCID 179619694-[(E)-2-cyanoethenyl]-1-[2-(trityloxy)ethyl]-5-aminopyrazole

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a suspension of sodium hydride (60% dispersion in mineral oil, 3.46 g) in tetrahydrofuran (250 ml) was added dropwise diethyl(cyanomethyl)phosphonate (23.3 ml) under ice-cooling. The mixture was stirred under ice-cooling for 1 hour. To the reaction mixture was added a solution of 1-(2-triphenylmethyloxyethyl)-5-aminopyrazole-4-carbaldehyde (47.76 g) in tetrahydrofuran (250 ml) at room temperature. The mixture was stirred at room temperature for 5 hours and extracted with ethyl acetate. The extract was washed with aqueous sodium hydrogencarbonate solution, water and brine. The extract was dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The residue was triturated with diisopropyl ether and dried in vacuo to give 4-[(E)-2-cyanoethenyl]-1-[2-(trityloxy)ethyl]-5-aminopyrazole (59.38 g). 1H-NMR(DMSO-d6) δ3.13 (2H, t, J=4.9 Hz), 4.15 (2H, t, J=4.9 Hz), 5.59 (1H, d, J=16.3 Hz), 6.35 (2H, s), 7.0–7.4 (15H, m), 7.47 (1H, d, J=16.3 Hz), 7.63 (1H, s)

後処理

  1. temperaturecooling
  2. temperaturecooling for 1 hour
  3. stirringThe mixture was stirred at room temperature for 5 hours
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with aqueous sodium hydrogencarbonate solution, water and brine
  6. dry with materialThe extract was dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was triturated with diisopropyl ether
  10. customdried in vacuo

出典と根拠

ORDレコード
ord-b4f06b8e10e741989f141c5e6d2ccb57
出典データセット
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07179801B2

反応ノート

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