p-Toluenesulfonic acid → HCID 60077026、化合物

HRID 413409

反応式

HRID 413409 の反応式
C[C:2]1([CH3:11])[O:6][C@@H:5]([C:7]([O:9][CH3:10])=[O:8])[CH2:4][O:3]1.[C:12]([O:20]CC=O)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:10][O:9][C:7]([C@H:5]1[CH2:4][O:3][CH:2]([CH2:11][O:20][C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[O:6]1)=[O:8]

参加物

5

反応物 3

HCID 6101p-Toluenesulfonic acidHCID 853166Methyl (4R)-2,2-dimethyl-1,3-dioxolane-4-carboxylateHCID 10866664HCID 10866664、化合物

生成物 1

HCID 60077026HCID 60077026、化合物収率 81%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To a solution of methyl-α,β-isopropylidene-D-glycerate (II) (Fluka: registry # 52373-72-5), (9.76 g, 60.9 mmol, 1 eq) and benzoyloxyacetaldehyde I (10 g, 60.9 mmol, 1 eq) in toluene (20 mL) at 80° C., p-toluenesulfonic acid (PTSA) (460 mg, 2.4 mmol, 4 mol %) was added. The reaction flask was kept under vacuum for one hour and a distillate was collected (80-85° C.) during this period of time. The residue was then cooled to room temperature (RT) and purified by column chromatography on silica gel, using hexanes/ethyl acetate as eluent to produce 13.2 g (81%) of the title compound as a mixture of cis and trans isomers in a ratio of 3:1.

後処理

  1. distillationa distillate was collected (80-85° C.) during this period of time
  2. custompurified by column chromatography on silica gel

出典と根拠

ORDレコード
ord-c47028294e8d4dbdadf4c702b7dd847c
出典データセット
uspto-grants-2003_05
特許番号
US06566365B1

関連ノート

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