Sodium hydride → Methyl 1-[3-(2-dioxolanyl)-propoxy]-pyrazole-4-carboxylate

HRID 232018ノート

反応式

HRID 232018 の反応式
[H-].[Na+].[OH:3][N:4]1[CH:8]=[C:7]([C:9]([O:11][CH3:12])=[O:10])[CH:6]=[N:5]1.[H][H].Cl[CH2:16][CH2:17][CH2:18][CH:19]1[O:23][CH2:22][CH2:21][O:20]1>CN(C)C=O>[O:20]1[CH2:21][CH2:22][O:23][CH:19]1[CH2:18][CH2:17][CH2:16][O:3][N:4]1[CH:8]=[C:7]([C:9]([O:11][CH3:12])=[O:10])[CH:6]=[N:5]1

参加物

6

反応物 4

HCID 24758Sodium hydrideHCID 5520722-(3-Chloropropyl)-1,3-dioxolaneHCID 13823205methyl 1-hydroxy-1H-pyrazole-4-carboxylateHCID 178418361HCID 178418361、化合物

生成物 1

HCID 13823206Methyl 1-[3-(2-dioxolanyl)-propoxy]-pyrazole-4-carboxylate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

21.8 g of sodium hydride (80 percent strength suspension in mineral oil) is introduced into 1.5 l of dry dimethylformamide, and 90 g of methyl 1-hydroxypyrazole-4-carboxylate are added a little at a time to the stirred mixture. When the evolution of hydrogen is complete, stirring is continued for 30 minutes, after which 95.5 g of 2-(3-chloropropyl)-1,3-dioxolane are added dropwise and the mixture is kept at 120° C. for 10 hours. Thereafter, the dimethylformamide is distilled off under reduced pressure, the residue is taken up in methyl tertbutyl ether, and the solution is washed with water, boiled and evaporated down to give 151 g of a slightly colored oil which crystallizes completely. M.p. 40°-42° C. NMR (CDCl3): 7.82 s [1]; 7.70 s [1]; 4.50 t [1]; 4.39 t [2]; 3.85-3.95 m [4]; 3.80 s [3]; 1.75-1.95 m [4].

後処理

  1. additionare added a little at a time to the stirred mixture
  2. waitthe mixture is kept at 120° C. for 10 hours
  3. distillationThereafter, the dimethylformamide is distilled off under reduced pressure
  4. washthe solution is washed with water
  5. customevaporated down
  6. customto give 151 g of a slightly colored oil which
  7. customcrystallizes completely

出典と根拠

ORDレコード
ord-791b2994b05649d7bd5312224ebe8c00
出典データセット
uspto-grants-1989_07
特許番号
US04851410

反応ノート

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