Dichloromethane → methyl 6-hydroxy-1H-indole-2-carboxylate

HRID 1171214ノート

反応式

HRID 1171214 の反応式
ClCCl.[CH3:4][O:5][C:6]([C:8]1[NH:9][C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[C:12]([O:17]C)[CH:11]=2)=[O:7].B(Br)(Br)Br>O>[CH3:4][O:5][C:6]([C:8]1[NH:9][C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[C:12]([OH:17])[CH:11]=2)=[O:7]

参加物

5

反応物 3

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 688173Methyl-6-methoxy-2-indolecarboxylate

生成物 1

HCID 10535709methyl 6-hydroxy-1H-indole-2-carboxylate収率 85%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
0 °C

実験手順

To a dichloromethane (10 mL) solution of 6-methoxy-1H-indole-2-carboxylic acid methyl ester (500 mg, 2.44 mmol) was added boron tribromide (12.2 mL, 12.2 mmol) at −78° C., which was stirred for 50 minutes at 0° C. under nitrogen atmosphere. To the reaction solution was added water at 0° C. followed by extraction with ethyl acetate. The organic layer was washed with sat. NaCl followed by drying over anhydrous magnesium sulfate and filtering. The filtrate was concentrated under a reduced pressure and the residue was purified by silica gel column chromatography (heptane:ethyl acetate=1:1) to obtain the title compound (395 mg, 85%) as a white solid.

後処理

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with sat. NaCl
  3. dry with materialby drying over anhydrous magnesium sulfate
  4. filtrationfiltering
  5. concentrationThe filtrate was concentrated under a reduced pressure
  6. customthe residue was purified by silica gel column chromatography (heptane:ethyl acetate=1:1)

出典と根拠

ORDレコード
ord-a9cc46d590d244bd960aafe109635e17
出典データセット
uspto-grants-2010_11
特許番号
US07829585B2

反応ノート

読み込み中…