2-Methylbenzenesulfonic acid → 2-Phthalimidoethyl acetoacetate

HRID 256721

反応式

HRID 256721 の反応式
[OH:1][CH2:2][CH2:3][N:4]1[C:8](=[O:9])[C:7]2=[CH:10][CH:11]=[CH:12][CH:13]=[C:6]2[C:5]1=[O:14].[CH3:15][C:16]1[O:22]C(C)(C)O[C:18](=[O:19])[CH:17]=1.C1(C)C(S(O)(=O)=O)=CC=CC=1>C1(C)C=CC=CC=1>[C:18]([O:1][CH2:2][CH2:3][N:4]1[C:8](=[O:9])[C:7]2=[CH:10][CH:11]=[CH:12][CH:13]=[C:6]2[C:5]1=[O:14])(=[O:19])[CH2:17][C:16]([CH3:15])=[O:22]

参加物

5

反応物 3

HCID 69252-Methylbenzenesulfonic acidHCID 77499N-(2-Hydroxyethyl)phthalimideHCID 793682,2,6-Trimethyl-4H-1,3-dioxin-4-one

生成物 1

HCID 114031062-Phthalimidoethyl acetoacetate収率 76.4%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A solution of 10.0 g (52.3 mmol) of N-(2-hydroxyethyl)phthalimide, 8.84 ml (67.7 mmol) of 2,2,6-trimethyl-1,3-dioxen-4-one, and 10 mg of p toluenesulfonic acid in 50 ml of toluene is heated at reflux under N2 for 4 hr. The solvent is removed under vacuum and the dark-colored residue is flash chromatographed on silica gel (1:1 hexane-EtOAc). The resulting product is recrystallized from EtOAc to give 11.0 g of 2-phthalimidoethyl acetoacetate.

後処理

  1. temperatureat reflux under N2 for 4 hr
  2. customThe solvent is removed under vacuum
  3. customchromatographed on silica gel (1:1 hexane-EtOAc)
  4. customThe resulting product is recrystallized from EtOAc

出典と根拠

ORDレコード
ord-7987d50d9c2949d8bba937edd21fb7c1
出典データセット
uspto-grants-1993_11
特許番号
US05258519

関連ノート

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