p-Toluenesulfonic acid → N-(2-hydroxy-3-n-propyl-4-methoxybenzoyl)thiazolidine

HRID 465914ノート

反応式

HRID 465914 の反応式
COC[O:4][C:5]1[C:17]([CH2:18][CH2:19][CH3:20])=[C:16]([O:21][CH3:22])[CH:15]=[CH:14][C:6]=1[C:7]([N:9]1[CH2:13][CH2:12][S:11][CH2:10]1)=[O:8].C1(C)C=CC(S(O)(=O)=O)=CC=1>CO.O>[OH:4][C:5]1[C:17]([CH2:18][CH2:19][CH3:20])=[C:16]([O:21][CH3:22])[CH:15]=[CH:14][C:6]=1[C:7]([N:9]1[CH2:13][CH2:12][S:11][CH2:10]1)=[O:8]

参加物

5

反応物 2

HCID 6101p-Toluenesulfonic acidHCID 14719505N-(2-methoxymethoxy-3-n-propyl-4-methoxybenzoyl)thiazolidine

生成物 1

HCID 14719506N-(2-hydroxy-3-n-propyl-4-methoxybenzoyl)thiazolidine収率 93.8%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

反応条件

温度
60 °C

実験手順

The N-(2-methoxymethoxy-3-n-propyl-4-methoxybenzoyl)thiazolidine (9.0 g) was dissolved in a solution of methanol (100 ml)-water (20 ml). To the solution was added p-toluenesulfonic acid (2 spoonfuls in spatula) and the mixture was agitated at 60° C. for 23 hours. The reaction mixture was concentrated in evacuated atomosphere to about one fourth of the original volume. Saturated aqueous solution of sodium bicarbonate was added to the concentrate, and the mixture was extracted twice with ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and concentrated in evacuated atomosphere. The residue was subjected to column chromatography using silica gel, and there was obtained N-(2-hydroxy-3-n-propyl-4-methoxybenzoyl)thiazolidine (7.3 g) from fractions eluted with n-hexane-ethyl acetate (5:1).

後処理

  1. concentrationThe reaction mixture was concentrated in evacuated atomosphere to about one fourth of the original volume
  2. additionSaturated aqueous solution of sodium bicarbonate was added to the concentrate
  3. extractionthe mixture was extracted twice with ethyl acetate
  4. washThe organic layer was washed with saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in evacuated atomosphere

出典と根拠

ORDレコード
ord-47637f04ae004b55b5939e8662ce861e
出典データセット
uspto-grants-1992_10
特許番号
US05155106

反応ノート

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