Water → 2-Hydroxymethyl-2,3-dihydro-thieno[3,4-b][1,4]dioxine-5,7-dicarboxylic acid

HRID 857812ノート

反応式

HRID 857812 の反応式
C[O:2][C:3]([C:5]1[S:6][C:7]([C:19]([O:21]C)=[O:20])=[C:8]2[C:13]=1[O:12][CH2:11][CH:10]([CH2:14][O:15]C(=O)C)[O:9]2)=[O:4].[OH-].[K+].O>C(O)C>[OH:15][CH2:14][CH:10]1[O:9][C:8]2=[C:7]([C:19]([OH:21])=[O:20])[S:6][C:5]([C:3]([OH:4])=[O:2])=[C:13]2[O:12][CH2:11]1

参加物

5

反応物 3

HCID 962Water2 回HCID 14797Potassium HydroxideHCID 207580182-Acetoxymethyl-2,3-dihydro-thieno[3,4-b][1,4]dioxine-5,7-dicarboxylic acid dimethyl ester

生成物 1

HCID 219583572-Hydroxymethyl-2,3-dihydro-thieno[3,4-b][1,4]dioxine-5,7-dicarboxylic acid

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

2-Acetoxymethyl-2,3-dihydro-thieno[3,4-b][1,4]dioxine-5,7-dicarboxylic acid dimethyl ester (60 g, 0.18 mol) was dissolved in ethanol (680 mL). KOH (36 g) was added to this solution after which water (500 mL) was added upon continuous cooling. After addition of the water the reaction mixture was stirred for another 30 minutes after which the solvents were removed by distillation. To the remaining part of the reaction mixture, we dropwise added a mixture of ice (50 g) and concentrated HCl (25 mL), and stirred. The mixture was then filtered and the residue was washed with water. Subsequent drying resulted in quantitative formation of pure 2-hydroxymethyl-2,3-dihydro-thieno[3,4-b][1,4]dioxine-5,7-dicarboxylic acid as demonstrated by NMR and mass spectroscopy.

後処理

  1. additionwas added upon continuous cooling
  2. customwere removed by distillation
  3. additionTo the remaining part of the reaction mixture, we dropwise added
  4. additiona mixture of ice (50 g) and concentrated HCl (25 mL)
  5. stirringstirred
  6. filtrationThe mixture was then filtered
  7. washthe residue was washed with water
  8. customSubsequent drying

出典と根拠

ORDレコード
ord-02a690062b594ace88eacd0bd82066e4
出典データセット
uspto-grants-2006_12
特許番号
US07147936B2

反応ノート

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