Imidazole → 4-(1-((tert-butyldiphenylsilyl)oxy)ethyl)-1H-1,2,3-triazole

HRID 708521ノート

反応式

HRID 708521 の反応式
[NH:1]1[CH:5]=[C:4]([CH:6]([OH:8])[CH3:7])[N:3]=[N:2]1.N1C=CN=C1.[CH3:14][C:15]([Si:18](Cl)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([CH3:17])[CH3:16]>C(Cl)Cl>[Si:18]([O:8][CH:6]([C:4]1[N:3]=[N:2][NH:1][CH:5]=1)[CH3:7])([C:15]([CH3:17])([CH3:16])[CH3:14])([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

参加物

5

反応物 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 178467229HCID 178467229、化合物

生成物 1

HCID 1784771794-(1-((tert-butyldiphenylsilyl)oxy)ethyl)-1H-1,2,3-triazole収率 46.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 1-(1H-1,2,3-triazol-4-yl)ethanol (50.2 mmol) and imidazole (5.13 mg, 75 mmol) in DCM (50 ml) 0° C. was added TBDPSCl (14.6 mL, 55.2 mmol). After stirring at room temperature overnight the mixture was filtered through a celite pad and then concentrated to dryness. The resulting residue was dissolved in EtOAc, washed with water, brine, dried with sodium sulfate and concentrated. Purification of the crude residue via silica gel chromatography (EtOAc-Heptane, 5-25%) afforded the title compound (8.16 g, 46%) as a yellow oil. LCMS: Rt=1.09 min, m/z=352.1 (M+1) Method 2m_acidic. 1H NMR (400 MHz, CDCl3) δ ppm 7.71 (d, J=6.5 Hz, 2H) 7.64-7.54 (m, 3H) 7.49-7.28 (m, 6H) 5.14 (q, J=6.3 Hz, 1H) 1.46 (dd, J=6.3, 3.0 Hz, 3H) 1.08 (s, 9H).

後処理

  1. filtrationwas filtered through a celite pad
  2. concentrationconcentrated to dryness
  3. dissolutionThe resulting residue was dissolved in EtOAc
  4. washwashed with water, brine
  5. dry with materialdried with sodium sulfate
  6. concentrationconcentrated
  7. customPurification of the crude residue via silica gel chromatography (EtOAc-Heptane, 5-25%)

出典と根拠

ORDレコード
ord-be53d2d5d4404d9f920cbf93abf304b2
出典データセット
uspto-grants-2015_11
特許番号
US09174978B2

反応ノート

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