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Acetic Acid → [4-[(E)-3-(3,4-Dichloro-phenyl)-acryloyl]-7-oxo-[1,4]diazepan-1-yl}-acetaldehyde

HRID 1867352
ノート
印刷プレビュー

反応式

HRID 1867352 の反応式
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Cl:7][C:8]1[CH:9]=[C:10](/[CH:15]=[CH:16]/[C:17]([N:19]2[CH2:25][CH2:24][C:23](=[O:26])[N:22]([CH2:27][C:28](N(OC)C)=[O:29])[CH2:21][CH2:20]2)=[O:18])[CH:11]=[CH:12][C:13]=1[Cl:14].CC(C)=O.C(O)(=O)C.OS([O-])(=O)=O.[K+]>C1COCC1>[Cl:7][C:8]1[CH:9]=[C:10](/[CH:15]=[CH:16]/[C:17]([N:19]2[CH2:25][CH2:24][C:23](=[O:26])[N:22]([CH2:27][CH:28]=[O:29])[CH2:21][CH2:20]2)=[O:18])[CH:11]=[CH:12][C:13]=1[Cl:14]
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

7

反応物 5

HCID 176Acetic AcidHCID 180AcetoneHCID 516920Potassium bisulfateHCID 21226445Aluminium lithium hydrideHCID 866158622-{4-[(E)-3-(3,4-Dichloro-phenyl)-acryloyl]-7-oxo-[1,4]diazepan-1-yl}-N-methoxy-N-methyl-acetamide

生成物 1

HCID 86615863[4-[(E)-3-(3,4-Dichloro-phenyl)-acryloyl]-7-oxo-[1,4]diazepan-1-yl}-acetaldehyde
収率 75.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-30 °C

実験手順

7.92 ml (7.92 mmol) of a LAH-solution (1.0 M in THF) was dropped to a cooled (−30° C.) suspension of 3.28 g (7.92 mmol) of 2-{4-[(E)-3-(3,4-dichloro-phenyl)-acryloyl]-7-oxo-[1,4]diazepan-1-yl}-N-methoxy-N-methyl-acetamide in 260 ml of THF. The reaction was stirred for 5 min at −30° C. and then cooled to −78° C. The reaction was stopped by adding first 12.8 ml (174.24 mmol) of acetone and afterwards 0.9 mL (15.84 mmol) of acetic acid. The reaction was then powered to an aqueous 10% KHSO4 solution and extracted with ether (3×), the organic phase was dried over Na2SO4 evaporated dissolved in toluene and evaporated (3×) to yield 2.12 g (75%) of the title compound as light yellow foam. MS: 355.0 (MH+, 2Cl).

後処理

  1. temperaturea cooled
  2. temperaturecooled to −78° C
  3. extractionextracted with ether (3×)
  4. dry with materialthe organic phase was dried over Na2SO4
  5. customevaporated
  6. dissolutiondissolved in toluene
  7. customevaporated (3×)

出典と根拠

ORDレコード
ord-aee5e64afe87435c86761fa4f4016760
出典データセット
uspto-grants-2009_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07632829B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート