Triethylamine → Coumarin, 3-(2-benzoylethyl)-4-hydroxy-

HRID 1721385

Reaktionsgleichung

Reaktionsgleichung von HRID 1721385
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][C:4](=[O:12])[CH:3]=1.CN(C)[CH:15]([CH3:24])[C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:17].C(N(CC)CC)C.[OH-].[Na+]>C(#N)C>[OH:1][C:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[O:5][C:4](=[O:12])[C:3]=1[CH2:24][CH2:15][C:16](=[O:17])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 71872MetamfepramoneHCID 546829304-Hydroxycoumarin

Produkt 1

HCID 54686119Coumarin, 3-(2-benzoylethyl)-4-hydroxy-

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A solution of 0.81 g (5.0 mmol) of 4-hydroxycoumarin, 1.07 g (5.0 mmol) of 2-dimethylaminopropiophenone, and 20 mL of acetonitrile was treated with 0.2 mL (5.0 mmol) of triethylamine and then refluxed for 4 hours. The mixture was cooled to room temperature and poured into 5% sodium hydroxide. The aqueous solution was extracted with ether and acidified to pH 3 with 6N hydrochloric acid. The mixture was extracted with chloroform, and the extract was washed with water, dried, and concentrated to give the title compound, m.p. 149°-151° C. NMR (CDCl3) δ2.99 (m, 2H), 3.52 (m, 2H), 7.26 (m, 2H), 7.48 (m, 3H), 7.60 (m, 1H), 7.94 (dd, 1H), 8.02 (d, 2H), 10.65 (bs, 1H).

Aufarbeitung

  1. temperaturerefluxed for 4 hours
  2. extractionThe aqueous solution was extracted with ether
  3. extractionThe mixture was extracted with chloroform
  4. washthe extract was washed with water
  5. customdried
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-f5b874ee69ea495dba5014bfe97c8f88
Quelldatensatz
uspto-grants-1996_04
Patentnummer
US05510375

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