Acetic Acid → Ethyl 2-(4,5-dichloro-2-hydroxyphenylamino)acetate

HRID 588768ノート

反応式

HRID 588768 の反応式
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([Cl:9])=[CH:4][C:3]=1[OH:10].[CH2:11]([O:13][C:14](=[O:17])[CH:15]=O)[CH3:12].CC(O)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[Cl:9][C:5]1[C:6]([Cl:8])=[CH:7][C:2]([NH:1][CH2:15][C:14]([O:13][CH2:11][CH3:12])=[O:17])=[C:3]([OH:10])[CH:4]=1

参加物

6

反応物 4

HCID 176Acetic AcidHCID 70211Ethyl oxoacetateHCID 30154152-Amino-4,5-dichlorophenolHCID 5049666Sodium triacetoxyborohydride

生成物 1

HCID 117610965Ethyl 2-(4,5-dichloro-2-hydroxyphenylamino)acetate収率 81%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 2-amino-4,5-dichlorophenol (2.0 g, 11.3 mmol) and ethyl-2-oxoacetate (2.26 g, 12.42 mmol) in DCM (50 mL) at room temperature, AcOH (1 mL) was added and the resulting mixture was stirred for 1 h. To this mixture, NaBH(OAc)3 (7.2 g, 33.9 mmol) was added and then stirred for 16 h. The mixture was concentrated in vacuo and the residue was suspended in DCM. The mixture was filtered through a pad of Celite and the filtrate was washed with brine. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (petroleum ether/ethyl acetate=10:1) to afford the desired product (2.4 g, 81% yield) as a solid.

後処理

  1. stirringstirred for 16 h
  2. concentrationThe mixture was concentrated in vacuo
  3. filtrationThe mixture was filtered through a pad of Celite
  4. washthe filtrate was washed with brine
  5. dry with materialThe organic layer was dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash column chromatography on silica gel (petroleum ether/ethyl acetate=10:1)

出典と根拠

ORDレコード
ord-0b276b5a9d03459dbf4f44630f146cfb
出典データセット
uspto-grants-2016_01
特許番号
US09227978B2

反応ノート

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