Triethylamine → [1-(4-Bromo-phenyl)-cyclobutoxy]-tert-butyl-dimethyl-silane

HRID 9234

반응식

HRID 9234 반응식
[Si:1]([O:8]S(C(F)(F)F)(=O)=O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Br:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2(O)[CH2:26][CH2:25][CH2:24]2)=[CH:19][CH:18]=1.C(N(CC)CC)C.C([O-])(O)=O.[Na+]>ClCCl>[Br:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2([O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH2:26][CH2:25][CH2:24]2)=[CH:19][CH:18]=1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 516892Sodium BicarbonateHCID 120954191-(4-Bromophenyl)cyclobutanol

생성물 1

HCID 21985972[1-(4-Bromo-phenyl)-cyclobutoxy]-tert-butyl-dimethyl-silane수율 93%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

TBSOTf (360 μL, 1.57 mmol) was added to a 0° C. solution of 3-1 (235 mg, 1.04 mmol) and triethylamine (450 μL, 3.23 mmol) in dichloromethane (3 mL). The reaction was allowed to warm to room temperature and after 1 h, saturated NaHCO3 solution was added. The resulting mixture was extracted with ethyl acetate (3×30 mL) and the combined ethyl acetate solution was washed with brine. The solution was then dried (Na2SO4), filtered and evaporated. Purification by flash chromatography on silica gel (hexanes) gave 3-2 (329 mg, 93%).

후처리

  1. extractionThe resulting mixture was extracted with ethyl acetate (3×30 mL)
  2. washthe combined ethyl acetate solution was washed with brine
  3. dry with materialThe solution was then dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customPurification by flash chromatography on silica gel (hexanes)

출처 및 근거

ORD 기록
ord-3369d74bfe9e4f18bb09dcce8d3f401e
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091231B2

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