(Methoxycarbonylsulfamoyl)triethylammonium hydroxide → Ethyl 4-[(7,8-dihydro-8,8-dimethylnaphth-2-yl)ethynyl]benzoate

HRID 277550

Reaktionsgleichung

O[CH:2]1[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:14]#[C:15][C:16]3[CH:26]=[CH:25][C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:18][CH:17]=3)[CH:5]=[CH:4][C:3]1=2.[OH-].COC(NS([N+](CC)(CC)CC)(=O)=O)=O>C1C=CC=CC=1>[CH3:13][C:9]1([CH3:12])[C:8]2[CH:7]=[C:6]([C:14]#[C:15][C:16]3[CH:17]=[CH:18][C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:25][CH:26]=3)[CH:5]=[CH:4][C:3]=2[CH:2]=[CH:11][CH2:10]1

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

To a solution of 0.13 g (0.38 mmol) of ethyl 4-[(5,6,7,8-tetrahydro-5-hydroxy-8,8-dimethylnaphth-2-yl)ethynyl]benzoate (Compound 9) in 15 ml of dry benzene was added 0.67 g (2.90 mmol) of (methoxycarbonylsulfamoyl) triethylammonium hydroxide (Burgess Reagent). The resulting mixture was heated at 50° C. for 30 minutes, cooled to room temperature, partitioned between water (10 ml) and EtOAc (20 ml) and the layers separated. The organic layer was dried over Na2SO4, concentrated in vacuo and purified by flash chromatography (silica, 10% EtOAc-hexane) to yield the title compound as a clear oil.

Aufarbeitung

temperaturecooled to room temperature
custompartitioned between water (10 ml) and EtOAc (20 ml)
customthe layers separated
dry with materialThe organic layer was dried over Na2SO4
concentrationconcentrated in vacuo
custompurified by flash chromatography (silica, 10% EtOAc-hexane)

Quellen und Nachweise

ORD-Eintrag: ord-18d88345c7dd4dc19ee35703fceb65f7
Quelldatensatz: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06355806B1

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