Chlorotrimethylsilane → HCID 59410091, 화합물

HRID 1805117노트

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HRID 1805117 반응식
[N+:1]([O-:4])([O-])=[O:2].[K+].C[Si](Cl)(C)C.[C:11](=[O:27])([O:25][CH3:26])[O:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH3:20])=[CH:15][C:14]=1[C:21]([CH3:24])([CH3:23])[CH3:22].[Al+3].[Cl-].[Cl-].[Cl-]>C(Cl)Cl>[C:11](=[O:27])([O:25][CH3:26])[O:12][C:13]1[CH:18]=[C:17]([N+:1]([O-:4])=[O:2])[C:16]([CH2:19][CH3:20])=[CH:15][C:14]=1[C:21]([CH3:22])([CH3:23])[CH3:24]

참가 물질

6

반응물 4

HCID 6397ChlorotrimethylsilaneHCID 24434Potassium NitrateHCID 6451240Aluminum(III) ChlorideHCID 59410128HCID 59410128, 화합물

생성물 1

HCID 59410091HCID 59410091, 화합물수율 70%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of KNO3 (3.9 g, 38.57 mmol) in DCM (50 mL) was added TMSCl (5.5 g, 50.62 mmol) and 2-tert-butyl-4-ethylphenyl methyl carbonate (6 g, 25.39 mmol) at 0° C. After stirring for 15 minutes, AlCl3 (10 g, 0.08 mol) was added and then the reaction mixture was stirred for 2 h. The reaction mixture was poured onto ice water and extracted with EtOAc (50 mL×3). The combined organic layers were dried over anhydrous Na2SO4, filtered and evaporated under vacuum to give the crude compound, which was purified by silica gel column chromatography (10-15% EtOAc in petroleum ether as eluant) to yield 2-tert-butyl-4-ethyl-5-nitrophenyl methyl carbonate (5 g, 70%). 1H NMR (400 MHz, CDCl3) 7.69 (s, 1H), 7.25 (s, 1H), 3.82 (s, 3H), 2.54 (q, J=7.6 Hz, 2H), 1.26 (s, 9H), 1.15 (d, J=7.6 Hz, 3H).

후처리

  1. stirringthe reaction mixture was stirred for 2 h
  2. additionThe reaction mixture was poured onto ice water
  3. extractionextracted with EtOAc (50 mL×3)
  4. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customevaporated under vacuum
  7. customto give the crude compound, which
  8. customwas purified by silica gel column chromatography (10-15% EtOAc in petroleum ether as eluant)

출처 및 근거

ORD 기록
ord-b042b753a4c7460d9337bb4d482a2cfb
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08354427B2

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