Triethylamine → HCID 90238349, compound

HRID 523342Notes

Reaction equation

HRID 523342 reaction equation
[CH2:1]([O:3][C:4](=[O:11])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][OH:10])[CH3:2].C(N(CC)CC)C.[C:19](Cl)(=[O:22])[CH:20]=[CH2:21]>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:11])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:19](=[O:22])[CH:20]=[CH2:21])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 357781Ethyl 6-hydroxyhexanoate

Product 1

HCID 90238349HCID 90238349, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of ethyl-6-hydroxyhexanoate (49.44 grams, 0.31 moles), methylene chloride (200 mL), and triethylamine (36.26 grams, 0.36 moles) was cooled in an ice bath. Acryloyl chloride (29.87 grams, 0.33 moles) was added dropwise over 60 minutes. The mixture was stirred for 3 hours and filtered. The solution was concentrated under vacuum and diluted with ethyl acetate (300 mL). The mixture was washed with saturated aqueous sodium bicarbonate and water, and then dried over magnesium sulfate. The solvent was removed under vacuum to give a crude oil that was purified by vacuum distillation. A slightly yellow oil (ethyl-6-acryloxy-hexanoate) was collected at 90-92° C. at 0.70 mm Hg (51.27 grams). A portion of this oil (40 grams) was further purified by column chromatography over silica gel using 10 volume percent ethyl acetate in hexane to give the product as a colorless oil.

Workup

  1. temperaturewas cooled in an ice bath
  2. filtrationfiltered
  3. concentrationThe solution was concentrated under vacuum
  4. additiondiluted with ethyl acetate (300 mL)
  5. washThe mixture was washed with saturated aqueous sodium bicarbonate and water
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was removed under vacuum
  8. customto give a crude oil that
  9. distillationwas purified by vacuum distillation
  10. customA slightly yellow oil (ethyl-6-acryloxy-hexanoate) was collected at 90-92° C. at 0.70 mm Hg (51.27 grams)
  11. customA portion of this oil (40 grams) was further purified by column chromatography over silica gel using 10 volume percent ethyl acetate in hexane

Sources & evidence

ORD record
ord-0825080357614c1f9b739e9ed11b111f
Source dataset
uspto-grants-2016_05
Patent number
US09334428B2

Reaction notes

Loading…