Water → HCID 86682561, compound

HRID 1469140Notes

Reaction equation

HRID 1469140 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7].[Cl:11][C:12](Cl)([O:14]C(=O)OC(Cl)(Cl)Cl)Cl.N1C=CC=CC=1.O>C(Cl)Cl>[Cl:11][C:12]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])=[O:14]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 94429TriphosgeneHCID 12917181Ethyl 5-hydroxypentanoate

Product 1

HCID 86682561HCID 86682561, compoundYield 179.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl 5-hydroxypentanoate (1.12 g, 7.66 mmol) was dissolved in 25 mL of methylene chloride, triphosgene (772 mg, 0.34 equivalent), and pyridine (0.743 mL, 1.2 equivalent) were sequentially added while stirred at 0° C., and the mixture was stirred at room temperature for 1 hour. After completion of the reaction, water was added, and extraction operation (methylene chloride) was performed. The separated organic layer was washed using an aqueous saturated sodium chloride solution, and dried with magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain the crude product. This was purified by column chromatography (ethyl acetate:n-hexane=1:10) to obtain the title compound (972 mg) having the following physical property values.

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hour
  2. additionwas added
  3. extractionextraction operation (methylene chloride)
  4. washThe separated organic layer was washed
  5. dry with materialdried with magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customto obtain the crude product
  8. customThis was purified by column chromatography (ethyl acetate:n-hexane=1:10)

Sources & evidence

ORD record
ord-a38eb0cbc66f43bf8ca5aabdc4c4077d
Source dataset
uspto-grants-2015_04
Patent number
US09006246B2

Reaction notes

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