Ethylene carbonate → HCID 18368357, compound

HRID 379703Notes

Reaction equation

HRID 379703 reaction equation
[OH:1][C:2]1[CH:16]=[CH:15][C:5]([NH:6][C:7]([CH:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[O:8])=[CH:4][CH:3]=1.C1(=O)O[CH2:20][CH2:19][O:18]1>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[OH:18][CH2:19][CH2:20][O:1][C:2]1[CH:3]=[CH:4][C:5]([NH:6][C:7]([CH:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[O:8])=[CH:15][CH:16]=1

Participants

5

Reactant 2

HCID 7303Ethylene carbonateHCID 18368265HCID 18368265, compound

Product 1

HCID 18368357HCID 18368357, compoundYield 89.6%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 962WaterSolvent

Conditions

Temperature
166 °C

Procedure

4′-Hydroxy-3,4,5,6-tetrahydro-2H-pyran-4-carboxanilide (13.5 g), ethylene carbonate (5.96 g) and tetrabutylammonium iodide (2.26 g) were combined and stirred for 2 hours at 166° C. After being cooled, the mixture was added with water (100 ml) and further mixed. Crystals formed were collected by filtration, washed with water and then dried under vacuum at 60° C. to obtain 4′-(2-hydroxyethoxy)-3,4,5,6-tetrahydro-2H-pyran-4-carboxanilide (14.5 g) as white crystal.

Workup

  1. temperatureAfter being cooled
  2. customCrystals formed
  3. filtrationwere collected by filtration
  4. washwashed with water
  5. customdried under vacuum at 60° C.

Sources & evidence

ORD record
ord-66bd27fc41ef4d0599311ac5ab8e47f1
Source dataset
uspto-grants-2001_10
Patent number
US06300368B1

Reaction notes

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