Sodium Chloride → HCID 54083712、化合物

HRID 382797

反応式

HRID 382797 の反応式
C([Li])CCC.[Br-].[CH2:7]([O:9][C:10]([CH2:12][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:11])[CH3:8].[CH2:32]([C:34]1[C:41]([O:42][CH3:43])=[CH:40][C:37]([CH:38]=O)=[CH:36][C:35]=1[O:44][CH3:45])[CH3:33].[Cl-].[Na+]>CCCCCC.O1CCCC1>[CH2:32]([C:34]1[C:41]([O:42][CH3:43])=[CH:40][C:37]([CH:38]=[CH:12][C:10]([O:9][CH2:7][CH3:8])=[O:11])=[CH:36][C:35]=1[O:44][CH3:45])[CH3:33]

参加物

7

反応物 4

HCID 5234Sodium ChlorideHCID 73731(Ethoxycarbonylmethyl)triphenylphosphonium bromideHCID 114468654-ethyl-3,5-dimethoxybenzaldehydeHCID 178418339Butyllithium

生成物 1

HCID 54083712HCID 54083712、化合物収率 79%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

実験手順

39.4 ml (63 mmol) of a 1.6N solution of n-butyllithium in hexane were added over a period of 15 minutes while stirring at −40° to a suspension of 28.3 g (66 mmol) of ethoxycarbonylmethyl-triphenylphosphonium bromide in 200 ml of tetrahydrofuran. The reaction mixture was stirred at 0° for one hour, cooled to −70° and treated dropwise over 30 minutes with a solution of 11.6 g (60 mmol) of 4-ethyl-3,5-dimethoxybenzaldehyde in 100 ml of tetrahydrofuran. Subsequently, the mixture was stirred at room temperature for a further 16 hours, poured into 600 ml of saturated sodium chloride solution and extracted twice with 800 ml of diethyl ether each time. The combined organic phases were washed once with 600 ml of saturated sodium chloride solution, dried (MgSO4) and concentrated in a vacuum. The crude product obtained was purified by column chromatography on silica gel (hexane/ethyl acetate 5:1). 12.5 g (79%) of ethyl 3-(4-ethyl-3,5-dimethoxy-phenyl)-acrylate were obtained as a white solid.

後処理

  1. temperaturecooled to −70°
  2. stirringSubsequently, the mixture was stirred at room temperature for a further 16 hours
  3. extractionextracted twice with 800 ml of diethyl ether each time
  4. washThe combined organic phases were washed once with 600 ml of saturated sodium chloride solution
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in a vacuum
  7. customThe crude product obtained
  8. customwas purified by column chromatography on silica gel (hexane/ethyl acetate 5:1)

出典と根拠

ORDレコード
ord-82487c62ba7046a68bc65611e170928a
出典データセット
uspto-grants-2001_10
特許番号
US06310208B1

関連ノート

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