Ethyl formate → 1,5,6,7-Tetrahydro-5-(hydroxymethylene)-1-methyl-4h-indazol-4-one

HRID 569907

反応式

HRID 569907 の反応式
[CH3:1][N:2]1[C:10]2[CH2:9][CH2:8][CH2:7][C:6](=[O:11])[C:5]=2[CH:4]=[N:3]1.[H-].[Na+].[CH:14](OCC)=[O:15]>C(O)C.C1(C)C=CC=CC=1>[OH:15][CH:14]=[C:7]1[CH2:8][CH2:9][C:10]2[N:2]([CH3:1])[N:3]=[CH:4][C:5]=2[C:6]1=[O:11]

参加物

6

反応物 3

HCID 8025Ethyl formateHCID 24758Sodium hydrideHCID 27657961-Methyl-1,5,6,7-tetrahydro-4H-indazol-4-one

生成物 1

HCID 571627141,5,6,7-Tetrahydro-5-(hydroxymethylene)-1-methyl-4h-indazol-4-one

試薬・触媒・溶媒 2

HCID 702Ethanol触媒HCID 1140Toluene溶媒

実験手順

A stirred mixture 16.8 grams of 1,5,6,7-tetrahydro-1-methyl-4H-indazol-4-one, 6 grams of 97% sodium hydride, 15 ml of ethyl formate, 3 drops of ethanol and 200 ml of toluene was heated at reflux for 16 hours. The mixture was then cooled and extracted twice with water and the aqueous extracts were combined and washed with ethyl ether. The aqueous solution was acidified with 5 N hydrochloric acid to a pH of approximately 4 and the resultant slurry was extracted several times with dichloromethane. The combined dichloromethane extracts were dried over magnesium sulfate and concentrated under reduced pressure to leave a residual dark oil. The oil was triturated with a 50:50 mixture of hexane and ethyl ether to give 1,5,6,7-tetrahydro-5-hydroxymethylene-1-methyl-4H-indazol-4-one melting at about 93°-95° C.

後処理

  1. temperatureat reflux for 16 hours
  2. temperatureThe mixture was then cooled
  3. extractionextracted twice with water
  4. washwashed with ethyl ether
  5. extractionthe resultant slurry was extracted several times with dichloromethane
  6. dry with materialThe combined dichloromethane extracts were dried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customto leave a residual dark oil
  9. customThe oil was triturated with a 50:50 mixture of hexane and ethyl ether

出典と根拠

ORDレコード
ord-7c61805d19484f8f8d96b5d159bb9db1
出典データセット
uspto-grants-1988_03
特許番号
US04734430

関連ノート

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