Dimethylformamide → 4-((Tert-butyldimethylsilyl)oxy)-4-methylpent-2-ynal

HRID 275517ノート

反応式

HRID 275517 の反応式
[C:1]([Si:5]([CH3:13])([CH3:12])[O:6][C:7]([CH3:11])([CH3:10])[C:8]#[CH:9])([CH3:4])([CH3:3])[CH3:2].[O:14]1CCC[CH2:15]1.CN(C)C=O>CCCCCC>[C:1]([Si:5]([CH3:13])([CH3:12])[O:6][C:7]([CH3:11])([CH3:10])[C:8]#[C:9][CH:15]=[O:14])([CH3:4])([CH3:3])[CH3:2]

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 11084826Silane, (1,1-dimethylethyl)[(1,1-dimethyl-2-propynyl)oxy]dimethyl-

生成物 1

HCID 108896204-((Tert-butyldimethylsilyl)oxy)-4-methylpent-2-ynal収率 78%

試薬・触媒・溶媒 1

HCID 8058Hexane溶媒

反応条件

温度
-78 °C

実験手順

To the solution of 10 g (50 mmol) of 3-(tert.butyldimethylsilyl)oxy-3-methyl-butyne in 25 ml. of anhydrous tetrahydrofuran cooled at -78° C. in an argon atmosphere was added dropwise over a 40 minute period 40 ml (0.64 mmol) 1.6M solution of N-butyl lithium in hexane, which was followed by addition of 31 ml (400 mmol) of N,N-dimethylformamide. The reaction mixture was stirred for an additional one-half hour at -78° C., and then quenched by addition of ice and pouring into 300 ml of brine. It was then extracted with pentane. The pentane extract was washed with saturated ammonium chloride solution, water and brine, dried over anhydrous sodium sulfate and evaporated to dryness. The crude product was purified by distillation at 113°-115° C./25 mmHg. It gave 8.88 g (78%) of the title compound.

後処理

  1. customquenched by addition of ice
  2. additionpouring into 300 ml of brine
  3. extractionIt was then extracted with pentane
  4. extractionThe pentane extract
  5. washwas washed with saturated ammonium chloride solution, water and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated to dryness
  8. distillationThe crude product was purified by distillation at 113°-115° C./25 mmHg

出典と根拠

ORDレコード
ord-a55b3810dc124a58bbac2f8ddb42a16a
出典データセット
uspto-grants-1995_02
特許番号
US05393900

反応ノート

読み込み中…