Sodium Hydroxide → 5-(6-phenylhexyl)-6,7-dihydro-5H-furo[3,2-c]pyridin-4-one

HRID 611429Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 611429
S(OCCC1OC=CC=1C(OC)=O)(C)(=O)=O.C1(CCCCCCN)C=CC=CC=1.[C:30]1([CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][N:42]2[C:46](=[O:47])[C:45]3=C[CH:49]=[CH:50][CH:51]=[C:44]3[C:43]2=[O:52])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.O.NN.[OH-].[Na+].C(N(CC)C(C)C)(C)C>C(O)C.C(#N)C.O>[C:30]1([CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][N:42]2[CH2:49][CH2:50][C:51]3[O:47][CH:46]=[CH:45][C:44]=3[C:43]2=[O:52])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Komponenten

10

Edukt 6

HCID 14798Sodium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 81531DiisopropylethylamineHCID 1455586-Phenylhexan-1-amineHCID 19599919N-(6-phenylhexyl)phthalimideHCID 19600087Methyl 2-(2-mesyloxyethyl)furan-3-carboxylate

Produkt 1

HCID 196001085-(6-phenylhexyl)-6,7-dihydro-5H-furo[3,2-c]pyridin-4-one

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A solution of the above crude methyl 2-(2-mesyloxyethyl)furan-3-carboxylate, crude 6-phenylhexylamine [prepared by refluxing a solution of 1.79 g (5.81 mmol) of N-(6-phenylhexyl)phthalimide and 0.28 ml (5.8 mmol) of hydrazine monohydrate in 20 ml of ethanol for 1 hour, cooling the reaction mixture to room temperature, then pouring it into aqueous sodium hydroxide, extracting with ethyl acetate 3 times, drying the combined organic layer over anhydrous magnesium sulfate, and distilling off the solvent] and 2.02 ml (11.6 mmol) of N,N-diisopropylethylamine in 50 ml of acetonitrile was refluxed for 3 days. The reaction mixture was poured into water and extracted with ethyl acetate 3 times. The combined organic layer was dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=6/1 to 3/1) to yield the desired product.

Aufarbeitung

  1. extractionextracting with ethyl acetate 3 times
  2. dry with materialdrying the combined organic layer over anhydrous magnesium sulfate
  3. temperaturewas refluxed for 3 days
  4. extractionextracted with ethyl acetate 3 times
  5. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=6/1 to 3/1)

Quellen und Nachweise

ORD-Eintrag
ord-c054cf3d45ef429785556fdf86b4affa
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US05998433

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