Triethylamine → alpha-(o-Fluorobenzoylthiomethyl)-beta-phenyl-gamma-butyrolactone

HRID 65262

Reaktionsgleichung

Reaktionsgleichung von HRID 65262
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[SH:11][CH2:12][CH:13]1[CH:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:17][O:16][C:14]1=[O:15].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.C(N(CC)CC)C>CN(C)C=O.C(OCC)C>[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([S:11][CH2:12][CH:13]1[CH:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:17][O:16][C:14]1=[O:15])=[O:6]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 99352-Fluorobenzoic acidHCID 199401P,P-Diphenylphosphinic azideHCID 13518975alpha-Mercaptomethyl-beta-phenyl-gamma-butyrolactone

Produkt 1

HCID 13518918alpha-(o-Fluorobenzoylthiomethyl)-beta-phenyl-gamma-butyrolactoneAusbeute 67,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 1.2 g of o-fluorobenzoic acid and 1.5 g of α-mercaptomethyl-β-phenyl-γ-butyrolactone in 20 ml of dimethylformamide were added 1.9 ml of diphenylphosphoryl azide (DPPA) and then 1.2 ml of triethylamine under ice-cooling. Then, the mixture was raised to a room temperature and stirred for 18 hours. After completion of the reaciton, the reaction mixture was diluted with 200 ml of ethyl ether, washed with 5% hydrochloric acid, saturated aqueous sodium hydrogencarbonate, and saturated saline, dried over magnesium sulfate and the solvent was then distilled off. The crude product thus obtained was purified by a silica gel column chromatography to give 1.6 g (yield 67%) of the title compound.

Aufarbeitung

  1. washwashed with 5% hydrochloric acid, saturated aqueous sodium hydrogencarbonate, and saturated saline
  2. dry with materialdried over magnesium sulfate
  3. distillationthe solvent was then distilled off
  4. customThe crude product thus obtained
  5. customwas purified by a silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-0a89f202a1ce4947b408e89c52abab67
Quelldatensatz
uspto-grants-1986_09
Patentnummer
US04613613

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