2,6-Lutidine → ((1-(4-Bromophenyl)hexyl)oxy)(tert-butyl)dimethylsilane

HRID 15003

반응식

HRID 15003 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]([CH:23](O)[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:19][CH:18]=1.N1C(C)=CC=CC=1C.C(=O)(O)[O-].[Na+]>ClCCl>[Br:16][C:17]1[CH:22]=[CH:21][C:20]([CH:23]([O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:19][CH:18]=1

참가 물질

6

반응물 4

HCID 79372,6-LutidineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 516892Sodium BicarbonateHCID 126030861-(4-Bromophenyl)hexan-1-ol

생성물 1

HCID 57438973((1-(4-Bromophenyl)hexyl)oxy)(tert-butyl)dimethylsilane수율 88.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

TBSOTf (2.9 mL, 12.6 mmol) was added to an ice-cold solution of 4 (3.017 g, 11.7 mmol) and 2,6-lutidine (1.6 mL, 13.7 mmol) in dichloromethane (30 mL). The reaction was stirred for 2 h at room temperature and then 100 mL saturated sodium bicarbonate solution was added. The resulting mixture was extracted with dichloromethane (30 mL) and the dichloromethane layer was washed with 1 M HCl (2×50 mL) and brine (50 mL). The dichloromethane solution was then dried (MgSO4), filtered and evaporated. Purification of the residue by flash chromatography on silica gel (hexanes) gave compound 5 (3.843 g, 88%).

후처리

  1. extractionThe resulting mixture was extracted with dichloromethane (30 mL)
  2. washthe dichloromethane layer was washed with 1 M HCl (2×50 mL) and brine (50 mL)
  3. dry with materialThe dichloromethane solution was then dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customPurification of the residue by flash chromatography on silica gel (hexanes)

출처 및 근거

ORD 기록
ord-57b752c626fb4e7bb2cebf81a4fdcceb
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732443B2

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