Pyridine → Chloromethyl (2,3,4,5-tetrahydrofurfuryl) carbonate

HRID 1370608Notes

Reaction equation

HRID 1370608 reaction equation
[CH2:1]([OH:7])[CH:2]1[O:6][CH2:5][CH2:4][CH2:3]1.N1C=CC=CC=1.Cl[C:15]([O:17][CH2:18][Cl:19])=[O:16]>CCOCC>[C:15](=[O:16])([O:7][CH2:1][CH:2]1[O:6][CH2:5][CH2:4][CH2:3]1)[O:17][CH2:18][Cl:19]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7360Tetrahydrofurfuryl alcoholHCID 62754Chloromethyl chloroformate

Product 1

HCID 17814605Chloromethyl (2,3,4,5-tetrahydrofurfuryl) carbonateYield 91.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Tetrahydrofurfuryl alcohol (19.4 g) was dissolved in anhydrous ether (500 ml) and, after adding pyridine (15 g) under ice cooling, chloromethyl chloroformate (25 g) was added dropwise. After the reaction mixture was stirred at room temperature for 17 hours, the deposited pyridine hydrochloride was removed by filtration and the filtrate was washed with ether (50 ml×2). The washings and the filtrate were combined, washed with water (300 ml×2) and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain chloromethyl (2,3,4,5-tetrahydrofurfuryl) carbonate (33.9 g) as a colorless oily product.

Workup

  1. customthe deposited pyridine hydrochloride was removed by filtration
  2. washthe filtrate was washed with ether (50 ml×2)
  3. washwashed with water (300 ml×2)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-a7f185a171ae46bdae625e57fa773113
Source dataset
uspto-grants-2003_06
Patent number
US06583164B1

Reaction notes

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