p-Toluenesulfonic acid monohydrate → Ethyl 4-[[(5,5-dimethyl-8-(carbethoxy)-5,6-dihydronaphthalen-2-yl)carbonyl]oxy]benzoate

HRID 1400

Reaktionsgleichung

Reaktionsgleichung von HRID 1400
[CH3:1][C:2]1([CH3:32])[CH2:11][CH2:10][C:9](O)([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:8]2[CH:7]=[C:6]([C:18]([O:20][C:21]3[CH:31]=[CH:30][C:24]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:23][CH:22]=3)=[O:19])[CH:5]=[CH:4][C:3]1=2.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH3:32][C:2]1([CH3:1])[CH2:11][CH:10]=[C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:8]2[CH:7]=[C:6]([C:18]([O:20][C:21]3[CH:22]=[CH:23][C:24]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:30][CH:31]=3)=[O:19])[CH:5]=[CH:4][C:3]1=2

Komponenten

4

Edukt 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 22571534(+/-) Ethyl 4-[[(5,5-dimethyl-8-hydroxy-8-(carbethoxy)-5,6,7,8-tetrahydronaphthalen-2-yl)carbonyl]oxy]benzoate

Produkt 1

HCID 22571524Ethyl 4-[[(5,5-dimethyl-8-(carbethoxy)-5,6-dihydronaphthalen-2-yl)carbonyl]oxy]benzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

To a solution of (±)ethyl 4-[[(5,5-dimethyl-8-hydroxy-8-(carbethoxy)-5,6,7,8-tetrahydronaphthalen-2-yl)carbonyl]oxy]benzoate (Compound E54, 35.0 mg, 0.077 mmol) in 10 mL benzene was added a catalytic amount (approximately 2 mg) of p-toluenesulfonic acid monohydrate. The solution was heated to reflux under a Dean-Stark trap for 3 h, and then cooled to room temperature and stirred overnight. The solvent was removed under reduced pressure and the title compound isolated from the residue by column chromatography (10% EtOAc-hexanes).

Aufarbeitung

  1. temperatureThe solution was heated
  2. temperatureto reflux under a Dean-Stark trap for 3 h
  3. customThe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-f22788fdfdc049bab420209786ecbc6d
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05723666

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