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

HRID 2221629노트

반응식

HRID 2221629 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6212Chloroform용매

반응 조건

온도
-40 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-35551a6a8c6b41a39e3e5918033e8db4
출처 데이터셋
uspto-grants-2008_05
특허 번호
US07368578B2

반응 노트

불러오는 중…