Triethylamine → (RS)-tert-Butyl-dimethyl-(4-oxiranylmethyl-phenoxy)-silane

HRID 1419930노트

반응식

HRID 1419930 반응식
[O:1]1[CH2:3][CH:2]1[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.[Si:12](Cl)([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13].C(N(CC)CC)C>C(Cl)Cl>[C:15]([Si:12]([CH3:14])([CH3:13])[O:11][C:8]1[CH:9]=[CH:10][C:5]([CH2:4][CH:2]2[CH2:3][O:1]2)=[CH:6][CH:7]=1)([CH3:18])([CH3:17])[CH3:16]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 53757927(RS)-4-Oxiranylmethyl-phenol

생성물 1

HCID 54376003(RS)-tert-Butyl-dimethyl-(4-oxiranylmethyl-phenoxy)-silane수율 82%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

(RS)-4-Oxiranylmethyl-phenol (1 g, 6.66 mmol) was dissolved in CH2Cl2 (50 ml) and stirred at room temperature in the presence of tert-butyldimethylsilyl chloride (1.3 g, 8.66 mmol), 4-dimethyl-aminopyridine (0.018 g, 0.15 mmol) and triethylamine (1.2 ml, 8.66 mmol). After 22 hours at room temperature, the reaction mixture was washed with H2O (2×100 ml) and the resulting aqueous phases were extracted with CH2Cl2 (100 ml). The combined organic phases were dried over Na2SO4 and concentrated. The residue was chromatographed over silica gel (hexane-ethylacetate 9:1) to provide (RS)-tert-Butyl-dimethyl-(4-oxiranylmethyl-phenoxy)-silane (1.44 g, 82%) as yellow oil, MS: m/e=264 (M+).

후처리

  1. washthe reaction mixture was washed with H2O (2×100 ml)
  2. extractionthe resulting aqueous phases were extracted with CH2Cl2 (100 ml)
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was chromatographed over silica gel (hexane-ethylacetate 9:1)

출처 및 근거

ORD 기록
ord-ba2cfacf52194902ac123bcf09f7faab
출처 데이터셋
uspto-grants-1999_03
특허 번호
US05889026

반응 노트

불러오는 중…