Water → HCID 15452329、化合物

HRID 356419ノート

反応式

HRID 356419 の反応式
[Li]CCCC.[CH2:6]([NH:8][C:9]([C:11]1[S:12][CH:13]=[CH:14][CH:15]=1)=[O:10])[CH3:7].[CH3:16][Si:17](Cl)([CH3:19])[CH3:18].O>CCCCCC.C1COCC1>[CH2:6]([NH:8][C:9]([C:11]1[S:12][C:13]([Si:17]([CH3:19])([CH3:18])[CH3:16])=[CH:14][C:15]=1[Si:17]([CH3:19])([CH3:18])[CH3:16])=[O:10])[CH3:7]

参加物

7

反応物 4

HCID 962WaterHCID 6397ChlorotrimethylsilaneHCID 5151566N-ethylthiophene-2-carboxamideHCID 178418339Butyllithium

生成物 1

HCID 15452329HCID 15452329、化合物

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒

反応条件

温度
-70 °C

実験手順

A solution of 2.5M n-BuLi in hexane (18 mL) was added dropwise to a solution of N-ethyl-2-thiophenecarboxamide (3.1 g, 20 mmol) in 50 mL THF at below -65° C. under a positive nitrogen atmosphere and the resulting solution was stirred at -70° C. for 45 min. After that, TMSCl (9 mL) was added slowly at below -60° C. and stirring was continued at below -60 ° C. for 15 min. The solution was allowed to warm to 0° C., then poured into water and extracted with CH2 Cl2. The organic layer was separated, washed with brine, dried and concentrated. Flash chromatography of the residue with 5% ethyl acetate-hexane yielded 3.1 g of Example 248 as a white solid, m.p. 81°-84° C., and 1.1 g of Example 249 as a colorless oil. nD24 1.5228.

後処理

  1. stirringstirring
  2. waitwas continued at below -60 ° C. for 15 min
  3. temperatureto warm to 0° C.
  4. extractionextracted with CH2 Cl2
  5. customThe organic layer was separated
  6. washwashed with brine
  7. customdried
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-2f56223b6e334a49917d11740b7b2b33
出典データセット
uspto-grants-1998_11
特許番号
US05834447

反応ノート

読み込み中…