Triethylamine → (S)-3-(t-butyldimethylsilyloxy)5bromo-1-phenyl pentane

HRID 23784

반응식

HRID 23784 반응식
[Si:1]([O:8][C@@H:9]([CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:10][CH2:11]O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(N(CC)CC)C.CS(Cl)(=O)=O.[Li+].[Br-:34]>ClCCl.O>[Si:1]([O:8][C@H:9]([CH2:10][CH2:11][Br:34])[CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 82050Lithium BromideHCID 69589993(S)-3-(t-butyldimethylsilyloxy)-5-phenyl-pentan-1-ol

생성물 1

HCID 67427479(S)-3-(t-butyldimethylsilyloxy)5bromo-1-phenyl pentane수율 86%

시약·촉매·용매 2

HCID 962Water용매2회HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

(S)-3-(t-butyldimethylsilyloxy)-5-phenyl-pentan-1-ol (10.6 g, 36 mmol) was dissolved in dichloromethane (80 ml), triethylamine (12.6 ml, 90.5 mmol) was added, and the mixture was cooled to 0° C. Methane sulfonyl chloride (4.2 ml, 54.3 mmol) was slowly added dropwise and the resulting mixture was stirred for 12 hours. After completion of the reaction, the reaction mixture was diluted with water (50 ml). The organic layer was separated and the aqueous layer was extracted with dichloromethane (50 ml×2). The organic layers were combined, washed with saturated aqueous NaCl solution, dried over MgSO4, filtered, and concentrated. Without further purification, the residue was dissolved in THF (60 ml). LiBr (7.86 g, 90.5 mmol) was added thereto and the mixture was refluxed for 4 hours. After completion of the reaction, water (80 ml) was added to the reaction solution which was then extracted with diethylether. The organic layers were combined, washed with saturated aqueous NaCl solution, dried over MgSO4, filtered, and concentrated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1) to give colorless and transparent (S)-3-(t-butyldimethylsilyloxy)-5-bromo-1-phenyl pentane (11 g. Yield 86%).

후처리

  1. customAfter completion of the reaction
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with dichloromethane (50 ml×2)
  4. washwashed with saturated aqueous NaCl solution
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customWithout further purification
  9. dissolutionthe residue was dissolved in THF (60 ml)
  10. temperaturethe mixture was refluxed for 4 hours
  11. additionwas added to the reaction solution which
  12. extractionwas then extracted with diethylether
  13. washwashed with saturated aqueous NaCl solution
  14. dry with materialdried over MgSO4
  15. filtrationfiltered
  16. concentrationconcentrated
  17. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1)
  18. customto give colorless

출처 및 근거

ORD 기록
ord-dc7a0e2b6eb946f498ff575e942a3f31
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06852880B2

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