Dimethyl Sulfate → 1,3-Dihydro-4-methoxy-1,3-dimethyl-2H-indol-2-one

HRID 1769

反応式

HRID 1769 の反応式
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]([CH3:13])[C:5](=[O:12])[N:6]2[CH3:11].[C:14](=O)([O-])[O-].[K+].[K+].COS(OC)(=O)=O>CC(C)=O>[CH3:14][O:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]([CH3:13])[C:5](=[O:12])[N:6]2[CH3:11]

参加物

5

反応物 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 196929451,3-dihydro-4-hydroxy-1,3-dimethyl-2H-indol-2-one

生成物 1

HCID 196929551,3-Dihydro-4-methoxy-1,3-dimethyl-2H-indol-2-one収率 86.2%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

A slurry of 1,3-dihydro-4-hydroxy-1,3-dimethyl-2H-indol-2-one (50 g), milled potassium carbonate (60.1 g) and HPLC grade acetone (400 ml) was mechanically stirred at room temperature as dimethylsulfate (41.4 ml) was added dropwise. The addition funnel was replaced with a condenser and the slurry was refluxed for 18 hours. The K2CO3 was filtered off and washed well with acetone. Acetone was evaporated and the residue was purified by column chromatography to yield 46.5 g of an oil. The oil was dissolved in ether and placed in the refrigerator where, upon standing overnight, the product crystallized, m.p. 73°-74° C.

後処理

  1. additionwas added dropwise
  2. customThe addition funnel was replaced with a condenser
  3. temperaturethe slurry was refluxed for 18 hours
  4. filtrationThe K2CO3 was filtered off
  5. washwashed well with acetone
  6. customAcetone was evaporated
  7. customthe residue was purified by column chromatography

出典と根拠

ORDレコード
ord-0f8c43802c60460ab93e17f76623a594
出典データセット
uspto-grants-1998_03
特許番号
US05726323

関連ノート

読み込み中…