Water → 3-(3-Benzyloxy-4-fluoro-phenylamino)-but-2-enoic acid ethyl ester

HRID 2415499ノート

反応式

HRID 2415499 の反応式
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([NH2:16])[CH:12]=[CH:13][C:14]=1[F:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17]([O:23][CH2:24][CH3:25])(=[O:22])[CH2:18][C:19]([CH3:21])=O.O.C([O-])(O)=O.[Na+]>C1CCCCC1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:24]([O:23][C:17](=[O:22])[CH:18]=[C:19]([NH:16][C:11]1[CH:12]=[CH:13][C:14]([F:15])=[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:10]=1)[CH3:21])[CH3:25]

参加物

7

反応物 4

HCID 962WaterHCID 8868Ethyl AcetoacetateHCID 516892Sodium BicarbonateHCID 226414853-Benzyloxy-4-fluoro-phenylamine

生成物 1

HCID 692871753-(3-Benzyloxy-4-fluoro-phenylamino)-but-2-enoic acid ethyl ester収率 100%

試薬・触媒・溶媒 2

HCID 521998p-Toluenesulfonic acid monohydrate触媒HCID 8078Cyclohexane溶媒

実験手順

92.7 g (0.43 mol) of 3-Benzyloxy-4-fluoro-phenylamine, 57 ml (0.45 mol) of ethyl acetoacetate and 0.81 g (4 mmol) of p-toluenesulfonic acid monohydrate in 370 ml of cyclohexane were heated at reflux for 3 h in the presence of a water separator funnel. The reaction mixture was cooled to RT, ACOEt (1 l) and saturated aqueous NaHCO3 solution (0.5 l) were added, the layers were separated and the organic layer once extracted with AcOEt (0.3 l). The combined organic layers were dried over magnesium sulfate and concentrated in vacuo to give 140 g (100%) of the desired 3-(3-benzyloxy-4-fluoro-phenylamino)-but-2-enoic acid ethyl ester as yellow-orange crystalline solid. Melting point: 79° C.-80° C.

後処理

  1. customthe layers were separated
  2. extractionthe organic layer once extracted with AcOEt (0.3 l)
  3. dry with materialThe combined organic layers were dried over magnesium sulfate
  4. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-5083ca4956e34c2cac1f041ff4076a48
出典データセット
uspto-grants-2004_11
特許番号
US06818767B2

反応ノート

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