Ethyl formate → 1-benzyl1,5,6,7-tetrahydro-5-hydroxymethylene 4H-indazol-4-one

HRID 569908ノート

反応式

HRID 569908 の反応式
[CH2:1]([N:8]1[C:16]2[CH2:15][CH2:14][CH2:13][C:12](=[O:17])[C:11]=2[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH:20](OCC)=[O:21].O1CCCC1>C(O)C.C(OCC)C.O>[CH2:1]([N:8]1[C:16]2[CH2:15][CH2:14][C:13](=[CH:20][OH:21])[C:12](=[O:17])[C:11]=2[CH:10]=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

8

反応物 4

HCID 8025Ethyl formateHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 47385581-benzyl-1,5,6,7-tetrahydro-4H-indazol-4-one

生成物 1

HCID 571673511-benzyl1,5,6,7-tetrahydro-5-hydroxymethylene 4H-indazol-4-one

試薬・触媒・溶媒 3

HCID 702Ethanol触媒HCID 962Water溶媒HCID 3283Diethyl Ether溶媒

実験手順

A mixture of 7.8 grams of 1-benzyl-1,5,6,7-tetrahydro-4H-indazol-4-one, 2.8 grams of sodium hydride (60% suspension in mineral oil), 10 ml of ethyl formate, 2 drops of ethanol and 100 ml of tetrahydrofuran was stirred at reflux for 1 hour and then cooled. Water (300 ml) and 100 ml of ethyl ether were added and the mixture was stirred briefly. The layers were separated and the aqueous layer was washed with ethyl ether and acidified with concentrated hydrochloric acid to a pH of about 4. The resulting slurry was extracted several times with dichloromethane and the combined organic extracts were dried over magnesium sulfate and concentrated under reduced pressure to give 1-benzyl1,5,6,7-tetrahydro-5-hydroxymethylene 4H-indazol-4-one as an amber oil.

後処理

  1. temperatureat reflux for 1 hour
  2. temperaturecooled
  3. stirringthe mixture was stirred briefly
  4. customThe layers were separated
  5. washthe aqueous layer was washed with ethyl ether
  6. extractionThe resulting slurry was extracted several times with dichloromethane
  7. dry with materialthe combined organic extracts were dried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-19f96bb143b64f6b9a8f0978546ca404
出典データセット
uspto-grants-1988_03
特許番号
US04734430

反応ノート

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