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

HRID 1269590ノート

反応式

HRID 1269590 の反応式
[CH:1]([C:3]1[CH:15]=[CH:14][C:6]([O:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:5]([CH3:16])[CH:4]=1)=O.[CH2:17]([NH2:21])[CH2:18][CH2:19][CH3:20].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)C>[CH2:17]([NH:21][CH2:1][C:3]1[CH:15]=[CH:14][C:6]([O:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:5]([CH3:16])[CH:4]=1)[CH2:18][CH2:19][CH3:20]

参加物

5

反応物 3

HCID 8007ButylamineHCID 5049666Sodium triacetoxyborohydrideHCID 58622891Ethyl (4-formyl-2-methylphenoxy)acetate

生成物 1

HCID 58622846Ethyl {4-[(butylamino)methyl]-2-methylphenoxy}acetate収率 68.9%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a solution of ethyl (4-formyl-2-methylphenoxy)acetate (3 g, 13.5 mmol) in anhydrous ethanol (50 mL) at room temperature, was added n-butylamine (1.6 mL, 16.2 mmol) and 4A molecular sieves. The resultant mixture was stirred at room temperature for 18 h under nitrogen, prior to portion wise addition of sodium triacetoxyborohydride (3.43 g, 16.2 mmol). After a further 3 h stirring at room temperature, the reaction was quenched by cautious addition of sat. sodium bicarbonate solution (40 mL) and then diluted with water (50 mL), before extracting with EtOAc (2×100 mL). The combined organic extracts were dried (MgSO4) and the solvents removed in vacuo, to afford the title compound as brown oil (2.6 g).

後処理

  1. customthe reaction was quenched by cautious addition of sat. sodium bicarbonate solution (40 mL)
  2. additiondiluted with water (50 mL)
  3. extractionbefore extracting with EtOAc (2×100 mL)
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. customthe solvents removed in vacuo

出典と根拠

ORDレコード
ord-b84e7ef73b164e4cb7221d2f1da49fde
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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