Imidazole → 4-((Triisopropylsilyloxy)methyl)thiazole

HRID 2071064

反応式

HRID 2071064 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 686703364-((Triisopropylsilyloxy)methyl)thiazole収率 84.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-d1897134dd9a41cca40357542317dec7
出典データセット
uspto-grants-2012_10
特許番号
US08299267B2

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