Butylamine → Ethyl {4-[(butylamino)methyl]-2-ethylphenoxy}acetate

HRID 1269666ノート

反応式

HRID 1269666 の反応式
[CH2:1]([C:3]1[CH:15]=[C:14]([CH:16]=O)[CH:13]=[CH:12][C:4]=1[O:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH3:2].[CH2:18]([NH2:22])[CH2:19][CH2:20][CH3:21]>C(O)C>[CH2:18]([NH:22][CH2:16][C:14]1[CH:13]=[CH:12][C:4]([O:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=[C:3]([CH2:1][CH3:2])[CH:15]=1)[CH2:19][CH2:20][CH3:21]

参加物

4

反応物 2

HCID 8007ButylamineHCID 58622859Ethyl (2-ethyl-4-formylphenoxy)acetate

生成物 1

HCID 58622897Ethyl {4-[(butylamino)methyl]-2-ethylphenoxy}acetate収率 56.4%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a solution of ethyl (2-ethyl-4-formylphenoxy)acetate (0.52 g, 2.2 mmol) in anhydrous ethanol (10 mL) was added butylamine (0.26 mL, 2.6 mmol). The resulting solution was stirred at room temperature under N2 for 18 h over 4A molecular sieves. The reaction was quenched by cautious addition of sat. NaHCO3 aq. (30 mL) and the mixture stirred for 30 mins. The mixture was then extracted EtOAc (2×100 mL). The combined organic extracts were dried (MgSO4), filtered and concentrated in vacuo. Purification by SPE (SCX, 20 g) conditioning the cartridge with ethanol and then loading the compound and washing with CH2Cl2, then ethanol before eluting the title compound using 10% NH3 in ethanol, evaporation of the 10% NH3 in ethanol extract afforded the title compound as a pale yellow oil (0.364 g).

後処理

  1. customThe reaction was quenched by cautious addition of sat. NaHCO3 aq. (30 mL)
  2. dry with materialThe combined organic extracts were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification by SPE (SCX, 20 g) conditioning the cartridge with ethanol
  6. washwashing with CH2Cl2
  7. washethanol before eluting the title compound
  8. custom10% NH3 in ethanol, evaporation of the 10% NH3 in ethanol
  9. extractionextract

出典と根拠

ORDレコード
ord-0ec592b03c4a40a1a5f42e1e8892965e
出典データセット
uspto-grants-2007_04
特許番号
US07199239B2

反応ノート

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