Toluene → Tert-butyl 4-(methoxycarbonyl)-3-nitrobenzoate

HRID 965275노트

반응식

HRID 965275 반응식
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([OH:12])=[O:11])=[CH:6][C:5]=1[N+:13]([O-:15])=[O:14].C(Cl)(=O)C(Cl)=O.[C:23]1([CH3:29])[CH:28]=CC=C[CH:24]=1>CN(C=O)C.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([O:12][C:23]([CH3:29])([CH3:28])[CH3:24])=[O:11])=[CH:6][C:5]=1[N+:13]([O-:15])=[O:14]

참가 물질

6

반응물 3

HCID 1140TolueneHCID 65578Oxalyl chlorideHCID 98592Methyl hydrogen 2-nitroterephthalate

생성물 1

HCID 23291046Tert-butyl 4-(methoxycarbonyl)-3-nitrobenzoate수율 83%

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 8857Ethyl Acetate용매

실험 절차

To a stirred suspension of the above acid ((6), 7.0 g, 31 mMol) in toluene (25 mL) was added oxalylchloride (5 mL) followed by one drop of dry DMF. After stirring for 16 h (the solution became clear after ~30 minutes) the reaction was evaporated to dryness and re-evaporated from fresh toluene (2×100 mL). To the resulting acid chloride in CHCl3 (10 mL) with stirring at 0° C. was added t-BuOH (1 mL) followed by pyridine (0.6 mL). The reaction was allowed to warm to room temperature and stirred for 6 h. The resulting reaction was stripped of solvent, taken up in ethyl acetate, washed with aq. 1N NaHCO3, brine, dried (MgSO4) and evaporated under reduced pressure. Purification by flash chromatography on silica gel eluted with 10% ethyl acetate in hexane gave product (7) (7.28 g, 83%) as a clear oil.

후처리

  1. waitbecame clear after ~30 minutes
  2. custom) the reaction was evaporated to dryness
  3. customre-evaporated from fresh toluene (2×100 mL)
  4. stirringTo the resulting acid chloride in CHCl3 (10 mL) with stirring at 0° C.
  5. additionwas added t-BuOH (1 mL)
  6. stirringstirred for 6 h
  7. customThe resulting reaction
  8. washwashed with aq. 1N NaHCO3, brine
  9. dry with materialdried (MgSO4)
  10. customevaporated under reduced pressure
  11. customPurification by flash chromatography on silica gel
  12. washeluted with 10% ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-cc3ce8af49464841adb81265b3a8f541
출처 데이터셋
uspto-grants-1998_06
특허 번호
US05773512

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