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Ammonium Chloride → Diisopropyl-4-(4-bromobenzyl)-1-ethoxycarbonyl-1,4-dihydropyridine-4-phosphonate

HRID 477049
ノート
印刷プレビュー

反応式

HRID 477049 の反応式
[CH:1]([O:4][P:5]([CH:11]1[CH:16]=[CH:15][N:14]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:13]=[CH:12]1)(=[O:10])[O:6][CH:7]([CH3:9])[CH3:8])([CH3:3])[CH3:2].C(=O)=O.CC(C)=O.C([Li])CCC.[Br:34][C:35]1[CH:42]=[CH:41][C:38]([CH2:39]Br)=[CH:37][CH:36]=1.[Cl-].[NH4+]>O1CCCC1.CCCCCC>[CH:7]([O:6][P:5]([C:11]1([CH2:39][C:38]2[CH:41]=[CH:42][C:35]([Br:34])=[CH:36][CH:37]=2)[CH:12]=[CH:13][N:14]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:15]=[CH:16]1)(=[O:10])[O:4][CH:1]([CH3:2])[CH3:3])([CH3:9])[CH3:8]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 25517Ammonium ChlorideHCID 685274-Bromobenzyl bromideHCID 11652617Diisopropyl-1-ethoxycarbonyl-1,4-dihydropyridine-4-phosphonateHCID 18522661Acetone cardiceHCID 178418339Butyllithium2 回

生成物 1

HCID 86743573Diisopropyl-4-(4-bromobenzyl)-1-ethoxycarbonyl-1,4-dihydropyridine-4-phosphonate
収率 60%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

実験手順

3.0 g of diisopropyl-1-ethoxycarbonyl-1,4-dihydropyridine-4-phosphonate was dissolved in 50 ml of tetrahydrofuran. The solution was cooled to -78° C. with a dry ice-acetone freezing mixture. In a stream of nitrogen, 6.8 ml of a hexane solution of n-butyllithium was slowly added dropwise. A solution of 2.50 g of p-bromobenzyl bromide in 10 ml of tetrahydrofuran was added dropwise. The temperature of the solution was returned to room temperature, and the solution was stirred for 20 hours. The excess of n-butyllithium was decomposed with ammonium chloride, and the solvent was evaporated. The residue was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium hydrogen carbonate, a saturated aqueous solution of sodium thiosulfate and a saturated aqueous solution of sodium chloride in this order, and the solvent was evaporated. The residue was subjected to silica gel column chromatography. The column was eluted with a 1:9 mixture of acetone and benzene to give 2.76 g (yield 56.6%) of diisopropyl-4-(4-bromobenzyl)-1-ethoxycarbonyl-1,4-dihydropyridine-4-phosphonate as a brown oil.

後処理

  1. customwas returned to room temperature
  2. customthe solvent was evaporated
  3. extractionThe residue was extracted with ethyl acetate
  4. washThe extract was washed with a saturated aqueous solution of sodium hydrogen carbonate
  5. customa saturated aqueous solution of sodium thiosulfate and a saturated aqueous solution of sodium chloride in this order, and the solvent was evaporated
  6. washThe column was eluted with a 1:9 mixture of acetone and benzene

出典と根拠

ORDレコード
ord-8c25b7c95574462b99287dc3b588fdf0
出典データセット
uspto-grants-1989_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04886822

反応ノート

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