Pyridine → Butyl ether

HRID 381222Notes

Reaction equation

HRID 381222 reaction equation
ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl.[CH2:13]([OH:21])[CH2:14][C:15]1[CH:20]=CC=CC=1.N1C=[CH:26][CH:25]=[CH:24][CH:23]=1>ClCCl>[CH2:23]([O:21][CH2:13][CH2:14][CH2:15][CH3:20])[CH2:24][CH2:25][CH3:26]

Participants

5

Reactant 3

HCID 1049PyridineHCID 60542-PhenylethanolHCID 94429Triphosgene

Product 1

HCID 8909Butyl ether

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 10.72 g triphosgene in 80 ml dichloromethane, 26.51 g phenethyl alcohol was added. While cooling in an ice bath, 17.16 g pyridine was dropped in over 45 minutes. Then, the reaction was stirred at room temperature for 62 hours. The reaction was diluted with dichloromethane, washed with aqueous HCl and aqueous NaHCO3. The organic phase was dried, filtered and evaporated to dryness. The resulting crystals were recrystallized from 60 ml hexanes and then a second time from hexane:methyl t.-butyl ether (50 ml:50 ml) to yield 15.48 g of colorless crystals.

Workup

  1. temperatureWhile cooling in an ice bath
  2. washwashed with aqueous HCl and aqueous NaHCO3
  3. customThe organic phase was dried
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe resulting crystals were recrystallized from 60 ml hexanes

Sources & evidence

ORD record
ord-a2408b413f2646d18f96c1e0059bbba8
Source dataset
uspto-grants-2001_10
Patent number
US06306818B1

Reaction notes

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