Trimethylsilyl triflate → HCID 10357417、化合物

HRID 1654782ノート

反応式

HRID 1654782 の反応式
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][C:12]=1[Br:13])[C:9](=[O:14])[CH2:8][CH2:7]2)([O-:3])=[O:2].C[Si](C)(C)[O:17][CH:18](O[Si](C)(C)C)[CH3:19].C[Si](OS(C(F)(F)F)(=O)=O)(C)C>C(Cl)Cl>[CH2:18]1[O:17][C:9]2([C:10]3[C:6](=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[C:12]([Br:13])[CH:11]=3)[CH2:7][CH2:8]2)[O:14][CH2:19]1

参加物

5

反応物 3

HCID 65367Trimethylsilyl triflateHCID 100609406-bromo-5-nitro-2,3-dihydro-1H-inden-1-oneHCID 18183672HCID 18183672、化合物

生成物 1

HCID 10357417HCID 10357417、化合物収率 79%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a suspension of 5-nitro-6-bromo-1-indanone (11.0 g, 43 mmol) and bis(trimethylsilyloxy)ethane (22.0 mL, 90 mmol) in CH2Cl2 (90 mL) at room temperature was added trimethylsilyltrifluoromethanesulfonate (100 μL). The mixture was stirred for 2 h and the homogeneous solution was quenched with saturated aqueous NaHCO3 (100 mL). The CH2Cl2 layer was separated, washed with brine, dried over anhydrous MgSO4 and concentrated in vacuo. Chromatography over silica gel, eluting with ethyl acetate:hexanes (2:5), furnished 10.2 g (79%) of the title compound as a pale yellow solid.

後処理

  1. customthe homogeneous solution was quenched with saturated aqueous NaHCO3 (100 mL)
  2. customThe CH2Cl2 layer was separated
  3. washwashed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated in vacuo
  6. washChromatography over silica gel, eluting with ethyl acetate:hexanes (2:5)

出典と根拠

ORDレコード
ord-5f5870a47b644ae68d7b679edc7fac00
出典データセット
uspto-grants-1995_04
特許番号
US05409944

反応ノート

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