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

HRID 1419930ノート

反応式

HRID 1419930 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

(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+).

後処理

  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)

出典と根拠

ORDレコード
ord-ba2cfacf52194902ac123bcf09f7faab
出典データセット
uspto-grants-1999_03
特許番号
US05889026

反応ノート

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