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Diisopropylethylamine → 6-Oxo-1-(2-trimethylsilanyl-ethoxymethyl)-1,6-dihydro-pyridazine-4-carboxylic acid ethyl ester

HRID 500538
ノート
印刷プレビュー

反応式

HRID 500538 の反応式
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][NH:9][C:10](=[O:12])[CH:11]=1)=[O:5])[CH3:2].C(N(C(C)C)CC)(C)C.Cl[CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28]>CN(C)C=O.CCOC(C)=O>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[C:10](=[O:12])[CH:11]=1)=[O:5])[CH3:2]
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

6

反応物 3

HCID 81531DiisopropylethylamineHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 12376258Ethyl 6-oxo-1,6-dihydropyridazine-4-carboxylate

生成物 1

HCID 248517026-Oxo-1-(2-trimethylsilanyl-ethoxymethyl)-1,6-dihydro-pyridazine-4-carboxylic acid ethyl ester収率 53.2%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

The title compound from Example 18.4 (0.90 g, 5.35 mmol) was stirred in dimethylformamide (20 mL) and diisopropyl ethylamine (1.39 mL, 8.025 mmol) at 0° C. and (2-chloromethoxy-ethyl)-trimethyl-silane (1.88 mL, 10.70 mmol) was added and the reaction was allowed to continue to stir at 0° C. for 2 hours and then overnight at r.t. The reaction mixture was diluted with EtOAc and washed with water and brine. The organic phase was dried over sodium sulfate, filtered and concentrated onto silica gel. The product was purified by column chromatography (0-20% EtOAc/hexanes) to afford the title compound as a clear oil (0.85 g, 53%).

後処理

  1. customovernight
  2. customat r.t
  3. washwashed with water and brine
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated onto silica gel
  7. customThe product was purified by column chromatography (0-20% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-56de719ec7044f52a82a8837ab42c978
出典データセット
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07772235B2

反応ノート

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