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

HRID 1808560ノート

反応式

HRID 1808560 の反応式
[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

参加物

5

反応物 3

HCID 7456MethylparabenHCID 11430Potassium Carbonate2 回HCID 758862-chloro-N,N-dimethylacetamide2 回

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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 (×2), brine (×3), 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)+.

後処理

  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 (×2), brine (×3)
  9. dry with materialdried (MgSO4)
  10. customevaporated

出典と根拠

ORDレコード
ord-bc74297baede4fbeab85d66b31ca767e
出典データセット
uspto-grants-2013_01
特許番号
US08357716B2

反応ノート

読み込み中…