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

HRID 708521노트

반응식

HRID 708521 반응식
[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

참가 물질

5

반응물 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 178467229HCID 178467229, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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%)

출처 및 근거

ORD 기록
ord-be53d2d5d4404d9f920cbf93abf304b2
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09174978B2

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