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

HRID 82816ノート

反応式

HRID 82816 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-a71a52c9f76a43e2910c52b2481e0fc6
出典データセット
uspto-grants-2014_09
特許番号
US08846733B2

反応ノート

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