(5,6-dichloro-1H-indol-2-yl)methanol → 5,6-dichloro-1H-indole-2-carbaldehyde

HRID 1070694ノート

反応式

HRID 1070694 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[Cl:11])[NH:7][C:6]([CH2:12][OH:13])=[CH:5]2>C(OCC)C.O=[Mn]=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[Cl:11])[NH:7][C:6]([CH:12]=[O:13])=[CH:5]2

参加物

4

反応物 1

HCID 22397554(5,6-dichloro-1H-indol-2-yl)methanol

生成物 1

HCID 108462775,6-dichloro-1H-indole-2-carbaldehyde収率 90.5%

試薬・触媒・溶媒 2

HCID 14801Manganese dioxide触媒2 回HCID 3283Diethyl Ether溶媒

実験手順

A solution of 5,6-dichloroindole-2-methanol (43 g, 199 mmol) in diethyl ether (1.3 l) was treated with activated MnO2 (64 g, 730 mmol) and stirred for 15 hours at room temperature. Additional MnO2 (20 g, 230 mmol) was added and stirring continued for 5 h. The suspension was filtered on a Celite pad, then the pad was washed with diethyl ether and warm acetone. The pooled organic phases were concentrated to give 38.5 g of the title compound (180 mmol, yield 90.4%) that was used as such in the next step, m.p.=207-208° C.

後処理

  1. stirringstirring
  2. waitcontinued for 5 h
  3. filtrationThe suspension was filtered on a Celite pad
  4. washthe pad was washed with diethyl ether
  5. temperaturewarm acetone
  6. concentrationThe pooled organic phases were concentrated

出典と根拠

ORDレコード
ord-d541b3ef956e44dcb99d55482b61dea7
出典データセット
uspto-grants-2005_06
特許番号
US06903117B2

反応ノート

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