Imidazole → 4-((Triisopropylsilyloxy)methyl)thiazole

HRID 2071064

반응식

HRID 2071064 반응식
[S:1]1[CH:5]=[C:4]([CH2:6][OH:7])[N:3]=[CH:2]1.[CH3:8][CH:9]([Si:11](Cl)([CH:15]([CH3:17])[CH3:16])[CH:12]([CH3:14])[CH3:13])[CH3:10].N1C=CN=C1>C(Cl)Cl>[CH:9]([Si:11]([CH:15]([CH3:17])[CH3:16])([CH:12]([CH3:14])[CH3:13])[O:7][CH2:6][C:4]1[N:3]=[CH:2][S:1][CH:5]=1)([CH3:10])[CH3:8]

참가 물질

5

반응물 3

HCID 795ImidazoleHCID 139400Triisopropylsilyl chlorideHCID 2763215(1,3-Thiazol-4-yl)methanol

생성물 1

HCID 686703364-((Triisopropylsilyloxy)methyl)thiazole수율 84.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a DCM solution of thiazol-4-ylmethanol (Combi-Blocks)(1 g, 8.69 mmol) stirred at 0° C., were added TIPSCl (2.2 mL, 10.43 mmol) and imidazole (1.48 g, 21.72 mmol). The resulting mixture was then warmed to room temperature and stirred for overnight. The reaction was quenched with saturated aqueous NH4Cl solution, extracted with ethyl acetate three times. The combined organic layers were washed with brine, dried with anhydrous Na2SO4, concentrated to a residue which was purified by flash column to give 4-((triisopropylsilyloxy)methyl)thiazole (2 g). 1H NMR (300 MHz, CDCl3), d: 8.794 (m, 1H), 7.338 (m, 1H), 5.065 (s, 2H), 1.209 (m, 3H), 1.133 (d, J=6 Hz, 18H).

후처리

  1. customThe reaction was quenched with saturated aqueous NH4Cl solution
  2. extractionextracted with ethyl acetate three times
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried with anhydrous Na2SO4
  5. concentrationconcentrated to a residue which
  6. customwas purified by flash column

출처 및 근거

ORD 기록
ord-d1897134dd9a41cca40357542317dec7
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08299267B2

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