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

HRID 3080
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인쇄 미리보기

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HRID 3080 반응식
[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]
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참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water
용매

반응 조건

온도
23 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e6001659ddac4b01bf370c708fa8cdd0
출처 데이터셋
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05733850

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