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

HRID 133109노트

반응식

HRID 133109 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-dcb414ecfee04c93870763d0454e2051
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07390820B2

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