1-Indanone → HCID 178419842、化合物

HRID 428622ノート

反応式

HRID 428622 の反応式
CN(C)S([N:6]1[CH:10]=[CH:9][N:8]=[CH:7]1)(=O)=O.C([Li])CCC.[Si](Cl)(C(C)(C)C)(C)C.[C:25]1(=O)[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:27][CH2:26]1>O1CCCC1.CCCCCC>[C:27]1([C:10]2[N:6]=[CH:7][NH:8][CH:9]=2)[C:28]2[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:25][CH:26]=1

参加物

7

反応物 4

HCID 67351-IndanoneHCID 28928tert-Butyldimethylsilyl chlorideHCID 395751N,N-Dimethyl-1H-imidazole-1-sulfonamideHCID 178418339Butyllithium2 回

生成物 1

HCID 178419842HCID 178419842、化合物

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒3 回HCID 8058Hexane溶媒2 回

反応条件

温度
25 °C

実験手順

To a stirred solution of 1-(N,N-dimethylsulfamoyl)-1H-imidazole (1.9 g, prepared according to Chadwick, D. J. and Ngochindo, R. I., J. Chem. Soc., Perkin Trans. I 1984, 481) in dry tetrahydrofuran (90 ml) at −70° C. under nitrogen, is added dropwise 2.5 M butyllithium in hexane (5.1 ml). After 30 minutes tert-butyldimethylsilyl chloride (2.0 g) in dry tetrahydrofuran (5 ml) is added and the mixture is allowed to warm to 25° C. After 1.5 hours the mixture is again cooled to −70° C. and treated with 2.5 M butyllithium in hexane (5.3 ml). After 30 minutes, 1-indanone (2.1 g) in dry tetrahydrofuran (5 ml) is added and the mixture is allowed to warm to room temperature. The reaction mixture is then quenched with saturated Na2CO3 solution (2 ml), and the solvent is removed under reduced pressure. The residue is dissolved in methylene chloride and washed with water, dried with sodium sufate and evaporated to dryness under reduced pressure. The bis-protected intermediate is refluxed with 2 N hydrochloric acid (200 ml) for 2 hours. The cooled solution is made basic by ammonium hydroxide solution, and extracted with methylene chloride. The organic layer is washed with water, dried with sodium sulfate and the solvent removed under reduced pressure. The crude product is purified by flash chromatography using methylene chloride-methanol as eluent. The product is converted to the hydrochloride salt in ethyl acetate-ethanol solution, m.p. 232-240° C.

後処理

  1. temperatureAfter 1.5 hours the mixture is again cooled to −70° C.
  2. temperatureto warm to room temperature
  3. customThe reaction mixture is then quenched with saturated Na2CO3 solution (2 ml)
  4. customthe solvent is removed under reduced pressure
  5. dissolutionThe residue is dissolved in methylene chloride
  6. washwashed with water
  7. dry with materialdried with sodium sufate
  8. customevaporated to dryness under reduced pressure
  9. temperatureThe bis-protected intermediate is refluxed with 2 N hydrochloric acid (200 ml) for 2 hours
  10. extractionextracted with methylene chloride
  11. washThe organic layer is washed with water
  12. dry with materialdried with sodium sulfate
  13. customthe solvent removed under reduced pressure
  14. customThe crude product is purified by flash chromatography

出典と根拠

ORDレコード
ord-4808bb73b8164d56baced2b32c48a741
出典データセット
uspto-grants-2001_11
特許番号
US06313311B1

反応ノート

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