Imidazole → (E)-4-(((tert-Butyldimethylsilyl)oxy)methyl)-2-styryloxazole

HRID 82816노트

반응식

HRID 82816 반응식
N#N.[CH:3](/[C:11]1[O:12][CH:13]=[C:14]([CH2:16][OH:17])[N:15]=1)=[CH:4]\[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[C:18]([Si:22](Cl)([CH3:24])[CH3:23])([CH3:21])([CH3:20])[CH3:19].N1C=CN=C1>C(Cl)Cl.O>[Si:22]([O:17][CH2:16][C:14]1[N:15]=[C:11](/[CH:3]=[CH:4]/[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:12][CH:13]=1)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:24])[CH3:23]

참가 물질

7

반응물 4

HCID 795ImidazoleHCID 947NitrogenHCID 28928tert-Butyldimethylsilyl chlorideHCID 13657827(E)-(2-Styryloxazol-4-yl)methanol

생성물 1

HCID 67958594(E)-4-(((tert-Butyldimethylsilyl)oxy)methyl)-2-styryloxazole

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of (E)-(2-styryloxazol-4-yl)methanol (5.40 g, 26.8 mmol) in CH2Cl2 (56.0 mL) was treated at rt with tert-butylchlorodimethylsilane (8.52 g, 53.67 mmol) followed by imidazole (3.69 g, 53.67 mmol) and the resulting suspension was stirred for 1 h at rt. Water was added. The aq. layer was extracted with and the combined org. layers were dried over Na2SO4, filtered and the solvent was removed under reduced pressure. Purification of the residue by FC (gradient from hept to 9:1 hept-EA) gave the title compound as a yellow oil. TLC: rf (9:1 hept-EA)=0.35. LC-MS-conditions 07: tR=1.08 min, [M+H]+=316.13.

후처리

  1. extractionThe aq. layer was extracted with and the combined org
  2. dry with materiallayers were dried over Na2SO4
  3. filtrationfiltered
  4. customthe solvent was removed under reduced pressure
  5. customPurification of the residue by FC (gradient from hept to 9:1 hept-EA)

출처 및 근거

ORD 기록
ord-a71a52c9f76a43e2910c52b2481e0fc6
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846733B2

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