Triethylamine → HCID 11746279, compound

HRID 2415418Notes

Reaction equation

HRID 2415418 reaction equation
[CH3:1][C@H:2]1[CH2:7][C@@H:6]([OH:8])[C@H:5]([CH:9]([CH3:11])[CH3:10])[CH2:4][CH2:3]1.[C:12](Cl)(=[O:16])[C:13]([CH3:15])=[CH2:14].C(N(CC)CC)C>ClCCl>[CH3:15][C:13](=[CH2:14])[C:12]([O:8][C@@H:6]1[CH2:7][C@H:2]([CH3:1])[CH2:3][CH2:4][C@H:5]1[CH:9]([CH3:11])[CH3:10])=[O:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13528Methacryloyl chlorideHCID 16666(-)-Menthol

Product 1

HCID 11746279HCID 11746279, compoundYield 73.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 100 ml flask, equipped with a magnetic stirrer, 5.0 g of L-(−)-menthol and 3.51 g of methacryloyl chloride were added to a solution of 6.67 ml of triethylamine in 30 ml of dichloromethane at room temperature. The clear solution turned turbid after a few minutes (exothermic reaction). After 4 hours, the suspension was extracted with 25 ml of 0.5 N HCl, 25 ml of water, 25 ml of saturated aqueous NaHCO3 and 25 ml of brine to give a clear orange solution (after drying over Na2SO4). Concentrating at reduced pressure gave a light brown/orange oil, which was stored overnight at 4° C. Purification by column chromatography (eluens: ethyl acetate/heptane=1/4) gave 5.30 g (73.8%) of a colourless oil. 1H-NMR confirmed the expected structure.

Workup

  1. customIn a 100 ml flask, equipped with a magnetic stirrer
  2. waitThe clear solution turned turbid after a few minutes
  3. custom(exothermic reaction)
  4. extractionthe suspension was extracted with 25 ml of 0.5 N HCl, 25 ml of water, 25 ml of saturated aqueous NaHCO3 and 25 ml of brine
  5. customto give
  6. dry with materiala clear orange solution (after drying over Na2SO4)
  7. concentrationConcentrating at reduced pressure
  8. customgave a light brown/orange oil, which
  9. waitwas stored overnight at 4° C
  10. customPurification by column chromatography (eluens: ethyl acetate/heptane=1/4)

Sources & evidence

ORD record
ord-edf71257284f4bb6b75df7e7b2241dc1
Source dataset
uspto-grants-2004_11
Patent number
US06818766B2

Reaction notes

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