Bromotrimethylsilane → [5-(Tert-butyldiphenylsilyloxymethyl)-2-phenyl-1,3-oxazol-4-yl]methanol

HRID 2221629ノート

反応式

HRID 2221629 の反応式
[Si:1]([O:18][CH2:19][C:20]1[O:24][C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[N:22][C:21]=1[CH2:31][O:32]COC)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si](Br)(C)C.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[Si:1]([O:18][CH2:19][C:20]1[O:24][C:23]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[N:22][C:21]=1[CH2:31][OH:32])([C:14]([CH3:15])([CH3:16])[CH3:17])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 76113BromotrimethylsilaneHCID 516892Sodium BicarbonateHCID 114886805-Tert-butyldiphenylsilyloxymethyl-4-methoxymethoxymethyl-2-phenyl-1,3-oxazole

生成物 1

HCID 11189974[5-(Tert-butyldiphenylsilyloxymethyl)-2-phenyl-1,3-oxazol-4-yl]methanol

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

反応条件

温度
-40 °C

実験手順

To a mixture of 5-tert-butyldiphenylsilyloxymethyl-4-methoxymethoxymethyl-2-phenyl-1,3-oxazole (20.0 g) and chloroform (250 mL) added dropwise trimethylsilyl bromide (25.0 g) at −40° C. The reaction mixture was stirred at −40° C. for 30 min, and the mixture was further stirred at room temperature for 1 hr. The reaction mixture was poured into saturated aqueous sodium hydrogen carbonate, and extracted with chloroform. The organic layer was dried over magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography and eluted with ethyl acetate-hexane (1:2, v/v) to give [5-(tert-butyldiphenylsilyloxymethyl)-2-phenyl-1,3-oxazol-4-yl]methanol. Recrystallization from hexane-ethyl acetate gave colorless crystals (10.2 g, yield 56%). melting point: 95-96° C.

後処理

  1. stirringthe mixture was further stirred at room temperature for 1 hr
  2. extractionextracted with chloroform
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated
  5. washeluted with ethyl acetate-hexane (1:2

出典と根拠

ORDレコード
ord-35551a6a8c6b41a39e3e5918033e8db4
出典データセット
uspto-grants-2008_05
特許番号
US07368578B2

反応ノート

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