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Sodium hydride → (S)-5'-fluoro-2,2-dimethylspiro[cyclopropane-1,3'-indolin]-2'-one

HRID 1805358
ノート
印刷プレビュー

反応式

HRID 1805358 の反応式
[H-].[Na+].[I-].[CH3:4][S+](C)(C)=O.[F:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][C:14](=[O:19])[C:13]2=[C:20]([CH3:22])[CH3:21]>CS(C)=O.O1CCCC1>[F:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][C:14](=[O:19])[C@@:13]12[CH2:21][C:20]1([CH3:4])[CH3:22]
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 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 672305505-Fluoro-3-isopropylidene-1,3-dihydro-indol-2-one

生成物 1

HCID 67230523(S)-5'-fluoro-2,2-dimethylspiro[cyclopropane-1,3'-indolin]-2'-one収率 85.6%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒
HCID 8028
Tetrahydrofuran
溶媒

反応条件

温度
50 °C

実験手順

A solution of NaH (60%) (0.6 g, 15 mmol) and trimethylsulfoxonium iodide (3.3 g, 15 mmol) in dimethyl sulfoxide (30 mL) was stirred for 30 minutes at 25° C. Then a solution of 5-fluoro-3-isopropylidene-1,3-dihydro-indol-2-one (2.6 g, 13.6 mmol) in dry tetrahydrofuran (30 mL) was added dropwise over 20 minutes. After being stirred for 1 hour at 25° C. and 1 hour at 50° C., the reaction solution was poured into ice-cold water and extracted with ether (3×100 mL), washed with water, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was recrystallized from ether to afford the title compound as white solid (2.39 g, 85%).

後処理

  1. additionthe reaction solution was poured into ice-cold water
  2. extractionextracted with ether (3×100 mL)
  3. washwashed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was recrystallized from ether

出典と根拠

ORDレコード
ord-96753d02d13640dbac5ab41cf9f1425e
出典データセット
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08354443B2

反応ノート

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