Pyridine → 6-Chloro-8-methylthiooctanoic acid ethyl ester

HRID 2291971ノート

反応式

HRID 2291971 の反応式
S(Cl)([Cl:3])=O.[CH2:5]([O:7][C:8](=[S:18])[CH2:9][CH2:10][CH2:11][CH2:12][CH:13](O)[CH2:14][CH2:15][CH3:16])[CH3:6].N1C=CC=CC=1>ClCCl>[CH2:5]([O:7][C:8](=[S:18])[CH2:9][CH2:10][CH2:11][CH2:12][CH:13]([Cl:3])[CH2:14][CH2:15][CH3:16])[CH3:6]

参加物

5

反応物 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 545259706-Hydroxy-8-methylthiooctanoic acid ethyl ester

生成物 1

HCID 536593926-Chloro-8-methylthiooctanoic acid ethyl ester収率 89.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

89.25 grams (0.7 mole) of thionyl chloride at +5° C. were slowly dropped into a solution of 137.0 grams (0.59 mole) of 6-hydroxy-8-methylthiooctanoic acid ethyl ester (VIb) and 1 ml of pyridine in 300 ml of dichloromethane. After stirring for 1 hour at +10° C. the mixture was heated for 3 hours at reflux and subsequently concentrated in a vacuum. The residue was treated with 200 ml of water and extracted with dichloromethane. After drying the combined extracts with sodium sulfate the solvent was removed in a vacuum. By fractional distillation there were obtained 125.1 grams (84% of theory) of 6-chloro-8-methylthiooctanoic acid ethyl ester as a colorless oil having a boiling point of 135° C. to 145° C. at 1 mbar.

後処理

  1. temperaturewas heated for 3 hours
  2. temperatureat reflux
  3. concentrationsubsequently concentrated in a vacuum
  4. additionThe residue was treated with 200 ml of water
  5. extractionextracted with dichloromethane
  6. dry with materialAfter drying the combined extracts with sodium sulfate the solvent
  7. customwas removed in a vacuum
  8. distillationBy fractional distillation there

出典と根拠

ORDレコード
ord-3d7f4ca18da545acb396e21d0d4c4af4
出典データセット
uspto-grants-1989_01
特許番号
US04800044

反応ノート

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