Water → tert-Butyl-[3-(4-chloro-benzenesulfonyl)-3-(2,3,6-trifluoro-phenyl)-propoxy]-dimethyl-silane

HRID 564300

반응식

HRID 564300 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:11][C:12]2[C:17]([F:18])=[C:16]([F:19])[CH:15]=[CH:14][C:13]=2[F:20])(=[O:10])=[O:9])=[CH:4][CH:3]=1.Br[CH2:22][CH2:23][O:24][Si:25]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26].[H-].[Na+].O>CN(C=O)C.C(OCC)(=O)C>[C:28]([Si:25]([O:24][CH2:23][CH2:22][CH:11]([S:8]([C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1)(=[O:10])=[O:9])[C:12]1[C:13]([F:20])=[CH:14][CH:15]=[C:16]([F:19])[C:17]=1[F:18])([CH3:27])[CH3:26])([CH3:31])([CH3:30])[CH3:29]

참가 물질

7

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilaneHCID 589503342-(4-Chloro-benzenesulfonylmethyl)-1,3,4-trifluoro-benzene

생성물 1

HCID 58950531tert-Butyl-[3-(4-chloro-benzenesulfonyl)-3-(2,3,6-trifluoro-phenyl)-propoxy]-dimethyl-silane

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

2-(4-Chloro-benzenesulfonylmethyl)-1,3,4-trifluoro-benzene (4.0 g, 12.5 mmol) was dissolved in 40 mL dry DMF. (2-Bromo-ethoxy)-tert-butyl-dimethylsilane (4.1 g, 17.1 mmol) and NaH (2.28 g, 95.0 mmol) were added respectively. The solution was stirred at room temperature overnight. 200 mL of water and 200 mL of EtOAc were added. The aqueous layer washed with 100 mL of EtOAc. The combined organic layers were washed with brine (100 mL), dried over Na2SO4 and concentrated. The product was purified using column chromatography (hex./EtOAc 100/0 to 90/10 in 45 min, 1.7 g, 28%). 1H NMR (CDCl3 400 MHz) δ 7.65 (m, 2H), 7.46 (m, 2H), 7.14 (m, 1H), 6.84 (m, 0.5H), 6.73 (m, 0.5H), 4.87 (m, 1H), 4.79 (m, 1H), 4.37 (m, 1H), 2.55 (m, 2H), 2.04 (s, 9H), −0.13 (d, J=22.7 Hz, 6H).

후처리

  1. washThe aqueous layer washed with 100 mL of EtOAc
  2. washThe combined organic layers were washed with brine (100 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe product was purified
  6. customcolumn chromatography (hex./EtOAc 100/0 to 90/10 in 45 min, 1.7 g, 28%)

출처 및 근거

ORD 기록
ord-e4ee02ee7b90463c8af2bef27578701b
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08067621B2

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