Chlorotrimethylsilane → HCID 59410091、化合物

HRID 1805117ノート

反応式

HRID 1805117 の反応式
[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]

参加物

6

反応物 4

HCID 6397ChlorotrimethylsilaneHCID 24434Potassium NitrateHCID 6451240Aluminum(III) ChlorideHCID 59410128HCID 59410128、化合物

生成物 1

HCID 59410091HCID 59410091、化合物収率 70%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-b042b753a4c7460d9337bb4d482a2cfb
出典データセット
uspto-grants-2013_01
特許番号
US08354427B2

反応ノート

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