2-Methylbenzenesulfonic acid hydrate → 5-(4-Chlorobenzyl)-2-chloromethyl-2-methyl-cyclopentanone

HRID 922739ノート

反応式

HRID 922739 の反応式
COC([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][Cl:12])([CH3:10])[C:6]1=[O:13])=O.O.C1(C)C(S(O)(=O)=O)=CC=CC=1>O>[Cl:21][C:18]1[CH:17]=[CH:16][C:15]([CH2:14][CH:5]2[C:6](=[O:13])[C:7]([CH2:11][Cl:12])([CH3:10])[CH2:8][CH2:9]2)=[CH:20][CH:19]=1

参加物

4

反応物 2

HCID 124969952-Methylbenzenesulfonic acid hydrateHCID 867182561-(4-Chlorobenzyl)-3-chloromethyl-3-methyl-2-oxo-cyclopentancarboxylic acid methyl ester

生成物 1

HCID 867182595-(4-Chlorobenzyl)-2-chloromethyl-2-methyl-cyclopentanone収率 91.3%

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

反応条件

温度
120 °C

実験手順

To 1.00 g of Compound 3-1-3 synthesized in Production Example 4, 0.578 g of toluenesulfonic acid monohydrate and 100 mg of water were added, and the resulting mixture was stirred in an oil bath of 120° C. for 1.5 hours. After the reaction, water was added to the reaction solution thus obtained, and extraction with ethyl acetate was then carried out. The extract was washed with an aqueous solution of sodium hydrogen carbonate and saturated brine. After the organic layer was dried over anhydrous sodium sulfate, the solvent was distilled away. The residue was purified by silica gel column chromatography to obtain 752 mg of Compound 4-1-3.

後処理

  1. additionwere added
  2. additionwas added to the reaction solution
  3. customthus obtained
  4. extractionextraction with ethyl acetate
  5. washThe extract was washed with an aqueous solution of sodium hydrogen carbonate and saturated brine
  6. dry with materialAfter the organic layer was dried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled away
  8. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-e83c17d032ee49ad9eed6a208d26cd9d
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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