Sodium Iodide → 2-Nitro-6-(2-oxoethyl)benzoic Acid Methyl Ester

HRID 133109ノート

反応式

HRID 133109 の反応式
[CH3:1][O:2][C:3](=[O:17])[C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[CH:6][C:5]=1[CH:13]=[CH:14][O:15]C.[Na+].[I-].C[Si](Cl)(C)C>CC#N>[CH3:1][O:2][C:3](=[O:17])[C:4]1[C:5]([CH2:13][CH:14]=[O:15])=[CH:6][CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11]

参加物

5

反応物 3

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 674228532-(2-Methoxyvinyl)-6-nitrobenzoic Acid Methyl Ester

生成物 1

HCID 866906922-Nitro-6-(2-oxoethyl)benzoic Acid Methyl Ester

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a solution of 2-(2-methoxy-vinyl)-6-nitro-benzoic acid methyl ester (Step A, 3.33 g, 14.1 mmol, 1.0 eq) and CH3CN (20 mL) was added NaI (2.3 g, 15.5 mmol, 1.1 eq) and TMSCl (2 mL, 15.5 mmol, 1.1 eq). The reaction was stirred at RT for 4 h, then quenched with saturated NH4Cl and extracted with EtOAc. The organic layer was washed with H2O and brine, dried (MgSO4) and concentrated in vacuo to give a red-orange oil. Purification by silica flash chromatography (0-30% EtOAc:hexane) gave the desired compound as an orange oil.

後処理

  1. customquenched with saturated NH4Cl
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with H2O and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customto give a red-orange oil
  7. customPurification by silica flash chromatography (0-30% EtOAc:hexane)

出典と根拠

ORDレコード
ord-dcb414ecfee04c93870763d0454e2051
出典データセット
uspto-grants-2008_06
特許番号
US07390820B2

反応ノート

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