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

HRID 3080
Notes
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Reaction equation

HRID 3080 reaction equation
[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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Conditions

Temperature
23 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-e6001659ddac4b01bf370c708fa8cdd0
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05733850

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes