Triethylamine → 4-[[[(1,1-Dimethylethyl)dimethylsilyl]oxy]methyl]thiazole

HRID 1028572

반응식

HRID 1028572 반응식
[S:1]1[CH:5]=[C:4]([CH2:6][OH:7])[N:3]=[CH:2]1.CCN(CC)CC.[Si:15](OS(C(F)(F)F)(=O)=O)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]>C(Cl)Cl.CCOC(C)=O>[Si:15]([O:7][CH2:6][C:4]1[N:3]=[CH:2][S:1][CH:5]=1)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 2763215(1,3-Thiazol-4-yl)methanol

생성물 1

HCID 667166624-[[[(1,1-Dimethylethyl)dimethylsilyl]oxy]methyl]thiazole

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

반응 조건

온도
-78 °C

실험 절차

To a solution of 1,3-thiazol-4-ylmethanol (311.4 mg, 2.7 mmol) in CH2Cl2 (15 mL) was added Et3N (1.9 mL, 13.6 mmol). The solution was cooled to −78° C. and TBSOTf (776 μL, 3.38 mmol) was added. The reaction was warmed to room temperature and stirred for 1 hour. Next, the reaction was diluted with EtOAc (75 mL) and washed with saturated NaHCO3, brine, 1N HCl, and brine (20 mL each). The organic layer was dried over Na2SO4, filtered, and concentrated. The residue was purified by flash chromatography on silica gel (0 to 15% EtOAc/hexanes) to afford 4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-1,3-thiazole. Rf=0.28 (15% EtOAc/hexanes). LCMS=230.1 (M+1)+. 1H NMR (CDCl3, 600 MHz) δ 8.77 (d, J=2.0 Hz, 1H), 7.25 (m, 1H), 4.93 (d, J=1.1 Hz, 2H), 0.95 (s, 9H), 0.12 (s, 6H).

후처리

  1. temperatureThe reaction was warmed to room temperature
  2. washwashed with saturated NaHCO3, brine, 1N HCl, and brine (20 mL each)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography on silica gel (0 to 15% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-dedf44e7fc53431ebdac3cff1e39026d
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08735435B2

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