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Pyridine → (+/-)-(3R,4S)-4-Acetoxy-3-(2-chloropropionyloxy)tetrahydrofuran

HRID 3080
ノート
印刷プレビュー

反応式

HRID 3080 の反応式
[Cl:1][CH:2]([CH3:6])[C:3](Cl)=[O:4].[OH:7][C@H:8]1[C@@H:12]([O:13][C:14]([CH3:16])=[O:15])[CH2:11][O:10][CH2:9]1.N1C=CC=CC=1.ClCCl>O>[C:14]([O:13][C@H:12]1[CH2:11][O:10][CH2:9][C@H:8]1[O:7][C:3](=[O:4])[CH:2]([Cl:1])[CH3:6])(=[O:15])[CH3:16]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 1110192-Chloropropionyl chlorideHCID 22883851(+/-)-(3R,4S)-3-hydroxy-4-methylcarbonyloxytetrahydrofuran

生成物 1

HCID 15789790(+/-)-(3R,4S)-4-Acetoxy-3-(2-chloropropionyloxy)tetrahydrofuran

試薬・触媒・溶媒 1

HCID 962Water
溶媒

反応条件

温度
23 °C

実験手順

12.4 g of (±)-2-chloropropionyl chloride were added dropwise at 0°-5° C. to an ice-cooled mixture of 15.0 g of (±)-(3R,4S)-3-hydroxy-4-methylcarbonyloxytetrahydrofuran, 8.1 g of anhydrous pyridine and 200 ml of anhydrous dichloromethane. After addition was complete, the reaction mixture was stirred at 23° C. for a further 4 hours, after which it was poured onto 400 ml of water. The organic phase was then separated off, washed twice with 50 ml of water each time, dried over sodium sulfate and finally concentrated. The crude product was purified by distillation at a pressure of 10 mbar.

後処理

  1. temperaturecooled
  2. additionAfter addition
  3. customThe organic phase was then separated off
  4. washwashed twice with 50 ml of water each time
  5. dry with materialdried over sodium sulfate
  6. concentrationfinally concentrated
  7. distillationThe crude product was purified by distillation at a pressure of 10 mbar

出典と根拠

ORDレコード
ord-e6001659ddac4b01bf370c708fa8cdd0
出典データセット
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05733850

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート