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Water → tert-Butyl(4-{[4-(4-chlorophenyl)-1-oxophthalazin-2(1H)-yl]methyl}phenyl)(cyclopentyl)acetate

HRID 877158
ノート
印刷プレビュー

反応式

HRID 877158 の反応式
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13](=[O:20])[NH:12][N:11]=2)=[CH:6][CH:5]=1.[C:21]([O:25][C:26](=[O:41])[CH:27]([C:33]1[CH:38]=[CH:37][C:36]([CH2:39]Br)=[CH:35][CH:34]=1)[CH:28]1[CH2:32][CH2:31][CH2:30][CH2:29]1)([CH3:24])([CH3:23])[CH3:22].O>C1COCC1.CN(C=O)C>[C:21]([O:25][C:26](=[O:41])[CH:27]([C:33]1[CH:38]=[CH:37][C:36]([CH2:39][N:12]2[N:11]=[C:10]([C:7]3[CH:6]=[CH:5][C:4]([Cl:3])=[CH:9][CH:8]=3)[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]2=[O:20])=[CH:35][CH:34]=1)[CH:28]1[CH2:32][CH2:31][CH2:30][CH2:29]1)([CH3:24])([CH3:23])[CH3:22]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 6890844-(4-Chlorophenyl)phthalazin-1-olHCID 15225592tert-Butyl 2-(4-(bromomethyl)phenyl)-2-cyclopentylacetate

生成物 1

HCID 58136552tert-Butyl(4-{[4-(4-chlorophenyl)-1-oxophthalazin-2(1H)-yl]methyl}phenyl)(cyclopentyl)acetate

試薬・触媒・溶媒 2

HCID 6228
Dimethylformamide
溶媒
HCID 8028Tetrahydrofuran溶媒

実験手順

At 0° C., 54 mg (2.14 mmol) of sodium hydride were added a little at a time to a solution of 500 mg (1.95 mmol) of 4-(4-chlorophenyl)phthalazin-1(2H)-one [CAS Reg. No. 51334-86-2] in 7.6 ml of THF. After the evolution of gas had ended, 688 mg (1.95 mmol) of tert-butyl[4-(bromomethyl)phenyl](cyclopentyl)acetate, dissolved in 4.5 ml of DMF, were slowly added dropwise at 0° C., and the reaction solution was then stirred at room temperature overnight. Water was then added carefully to the reaction mixture. The reaction mixture was extracted three times with ethyl acetate, and the combined organic phases were washed with saturated sodium chloride solution and dried over sodium sulfate. After filtration, the solvent was removed to dryness under reduced pressure. The crude product obtained was purified by flash chromatography on silica gel (mobile phase: initially cyclohexane/ethyl acetate 3:1, then ethyl acetate). This gave 630 mg (93% pure, 1.11 mmol, 57% of theory) of a colorless solid.

後処理

  1. additionwere slowly added dropwise at 0° C.
  2. extractionThe reaction mixture was extracted three times with ethyl acetate
  3. washthe combined organic phases were washed with saturated sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. filtrationAfter filtration
  6. customthe solvent was removed to dryness under reduced pressure

出典と根拠

ORDレコード
ord-d5d043e9a235408a9e959f1e03729cfa
出典データセット
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08987256B2

反応ノート

読み込み中…

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