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

HRID 275517노트

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HRID 275517 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8058Hexane용매

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온도
-78 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a55b3810dc124a58bbac2f8ddb42a16a
출처 데이터셋
uspto-grants-1995_02
특허 번호
US05393900

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