1-Methylimidazole → 1-(4-Chlorobenzyl)-3-(4-toluenesulfonyloxy)methyl-3-methyl-2-oxo-cyclopentancarboxylic acid methyl ester

HRID 922735ノート

反応式

HRID 922735 の反応式
[CH3:1][O:2][C:3]([C:5]1([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[CH2:9][CH2:8][C:7]([CH2:11][OH:12])([CH3:10])[C:6]1=[O:13])=[O:4].C(N(CC)CC)C.CN1C=CN=C1.[C:35]1([CH3:45])[CH:40]=[CH:39][C:38]([S:41](Cl)(=[O:43])=[O:42])=[CH:37][CH:36]=1>C1(C)C=CC=CC=1.O>[CH3:1][O:2][C:3]([C:5]1([CH2:14][C:15]2[CH:16]=[CH:17][C:18]([Cl:21])=[CH:19][CH:20]=2)[CH2:9][CH2:8][C:7]([CH2:11][O:12][S:41]([C:38]2[CH:39]=[CH:40][C:35]([CH3:45])=[CH:36][CH:37]=2)(=[O:43])=[O:42])([CH3:10])[C:6]1=[O:13])=[O:4]

参加物

7

反応物 4

HCID 13901-MethylimidazoleHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 672540121-(4-Chlorobenzyl)-3-hydroxymethyl-3-methyl-2-oxocyclopentanecarboxylic acid methyl ester

生成物 1

HCID 867182551-(4-Chlorobenzyl)-3-(4-toluenesulfonyloxy)methyl-3-methyl-2-oxo-cyclopentancarboxylic acid methyl ester収率 75.8%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1140Toluene溶媒

実験手順

In 95 ml of toluene, 4.756 g of Compound 2-1 obtained in Production Example 1 was dissolved. To the solution thus obtained, 3.12 ml of triethylamine and 1.76 ml of N-methylimidazole were added, and 3.38 g of 4-toluenesulfonyl chloride was added. The resulting mixture was stirred at room temperature for 100 minutes. After the reaction, water was added to the reaction solution thus obtained, and the organic layer was separated from the suspension. Thereafter, the aqueous layer was extracted with toluene and then blended with the organic layer previously obtained. The resultant organic layer thus obtained was washed with an aqueous solution of 1 mol/l hydrochloric acid and saturated brine and then dried over anhydrous sodium sulfate. The solvent was distilled away, and the residue was then purified by silica gel column chromatography to obtain 5.397 g of Compound 3-1-2.

後処理

  1. dissolutionwas dissolved
  2. customTo the solution thus obtained
  3. additionwas added to the reaction solution
  4. customthus obtained
  5. customthe organic layer was separated from the suspension
  6. extractionThereafter, the aqueous layer was extracted with toluene
  7. custompreviously obtained
  8. customThe resultant organic layer thus obtained
  9. washwas washed with an aqueous solution of 1 mol/l hydrochloric acid and saturated brine
  10. dry with materialdried over anhydrous sodium sulfate
  11. distillationThe solvent was distilled away
  12. customthe residue was then purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-b36ebe72e0254bafb75aae5438d2d478
出典データセット
uspto-grants-2016_03
特許番号
US09278966B2

反応ノート

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