Methylparaben → Methyl 4-{[2-(dimethylamino)-2-oxoethyl]oxy}benzoate

HRID 1874666노트

반응식

HRID 1874666 반응식
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:19][C:20]([N:22]([CH3:24])[CH3:23])=[O:21]>CN(C=O)C>[CH3:23][N:22]([CH3:24])[C:20](=[O:21])[CH2:19][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=1

참가 물질

5

반응물 3

HCID 7456MethylparabenHCID 11430Potassium Carbonate2회HCID 758862-chloro-N,N-dimethylacetamide2회

생성물 1

HCID 45792893Methyl 4-{[2-(dimethylamino)-2-oxoethyl]oxy}benzoate수율 68.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Methyl 4-hydroxybenzoate (Fluka) (1.52 g, 10 mmol) and potassium carbonate (1.38 g, 10 mmol) in DMF (10 mL) was treated with 2-chloro-N,N-dimethylacetamide (Merck) (1.03 ml, 10 mmol) and the mixture was stirred at RT overnight. The reaction mixture was worked up by partitioning between ethyl acetate and 2M hydrochloric acid, washing with HCl, brine, dried (MgSO4) and evaporating to dryness. The residue was dissolved in DMF (5 mL) and treated with potassium carbonate (1.38 g, 10 mmol) and 2-chloro-N,N-dimethylacetamide (Merck) (1.03 ml, 10 mmol). The mixture was stirred at RT over the weekend, and then worked up. Partitioned between ethyl acetate and 2M HCl and the organic solution was washed with HCl (X2), brine (X3), dried (MgSO4), and evaporated to give the title compound (1.62 g, 68%) as a white solid. LCMS (System A) RT=0.73 min, ES+ve m/z 238 (M+H)+.

후처리

  1. customby partitioning between ethyl acetate and 2M hydrochloric acid
  2. washwashing with HCl, brine
  3. dry with materialdried (MgSO4)
  4. customevaporating to dryness
  5. dissolutionThe residue was dissolved in DMF (5 mL)
  6. stirringThe mixture was stirred at RT over the weekend
  7. customPartitioned between ethyl acetate and 2M HCl
  8. washthe organic solution was washed with HCl (X2), brine (X3)
  9. dry with materialdried (MgSO4)
  10. customevaporated

출처 및 근거

ORD 기록
ord-b04181af892b4480bb12886a6abc2173
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08304446B2

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