Hydrochloric Acid → 4-Benzoyloxy-1-hydroxy-1-hexene-3,5-dione

HRID 466290ノート

反応式

HRID 466290 の反応式
C(NC(C)C)(C)C.C([Li])CCC.[C:13]([O:21][CH:22]([C:26](=[O:28])[CH3:27])[C:23](=[O:25])[CH3:24])(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[CH:29](OCC)=[O:30].Cl.[Cl-].[Na+]>O1CCCC1.CCCCCC>[C:13]([O:21][CH:22]([C:26](=[O:28])[CH3:27])[C:23](=[O:25])[CH:24]=[CH:29][OH:30])(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

参加物

9

反応物 6

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 7912DiisopropylamineHCID 8025Ethyl formateHCID 207383-(Benzoyloxy)-2,4-pentanedioneHCID 178418339Butyllithium

生成物 1

HCID 679144844-Benzoyloxy-1-hydroxy-1-hexene-3,5-dione収率 109.4%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

反応条件

温度
-78 °C

実験手順

Diisopropylamine (48.6 g, 480 mmol) is dissolved in 350 ml of tetrahydrofuran. At -40° C. there are added dropwise thereto 275 ml (440 mmol) of 1.6 molar butyl-lithium solution in hexane. The mixture is then cooled to -78° C. and 44.02 g (200 mmol) of 3-benzoyloxy-2,4-pentane-dione in 50 ml of tetrahydrofuran are added dropwise thereto within 30 minutes. Subsequently, 22.20 g (300 mmol) of ethyl formate are added dropwise thereto at -78° C. within 30 minutes and the mixture is stirred for 2 hours. The reaction mixture is poured into 600 ml of 1N hydrochloric acid, saturated with sodium chloride and extracted three times with 500 ml of ethyl acetate each time. The combined organic phases are dried over magnesium sulphate, concentrated on a rotary evaporator and give 54.30 g of 4-benzoyloxy-1-hydroxy-1-hexene-3,5-dione.

後処理

  1. additionAt -40° C. there are added dropwise
  2. waitat -78° C. within 30 minutes
  3. extractionextracted three times with 500 ml of ethyl acetate each time
  4. dry with materialThe combined organic phases are dried over magnesium sulphate
  5. concentrationconcentrated on a rotary evaporator

出典と根拠

ORDレコード
ord-ed8a631049cc409fa7b008e4c910f872
出典データセット
uspto-grants-1992_10
特許番号
US05155254

反応ノート

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