Ethyl 4-[(7,8-dihydro-8,8-dimethyl-5-(1,1-dimethylethyl)naphth-3-yl)ethynyl]benzoate → Ethyl 4-[(7,8-dihydro-8,8-dimethyl-5-(1,1-dimethylethyl)naphth-2-yl)ethynyl]benzoate

HRID 265795Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 265795
[CH3:1][C:2]1([CH3:29])C2C=CC(C#CC3C=CC(C(OCC)=O)=CC=3)=CC=2[C:5]([C:25]([CH3:28])([CH3:27])[CH3:26])=[CH:4][CH2:3]1.FC(F)(F)S(OC1[C:37]2[CH:38]=[CH:39][C:40]([C:48]#[C:49][C:50]3[CH:60]=[CH:59][C:53]([C:54]([O:56][CH2:57][CH3:58])=[O:55])=[CH:52][CH:51]=3)=[CH:41][C:42]=2C(C)(C)CC=1)(=O)=O>>[CH3:29][C:2]1([CH3:1])[C:38]2[CH:39]=[C:40]([C:48]#[C:49][C:50]3[CH:51]=[CH:52][C:53]([C:54]([O:56][CH2:57][CH3:58])=[O:55])=[CH:59][CH:60]=3)[CH:41]=[CH:42][C:37]=2[C:5]([C:25]([CH3:26])([CH3:27])[CH3:28])=[CH:4][CH2:3]1

Komponenten

3

Edukt 2

HCID 18314564Ethyl 4-[(7,8-dihydro-8,8-dimethyl-5-(1,1-dimethylethyl)naphth-3-yl)ethynyl]benzoate2×HCID 18314575Ethyl 4-[(5-trifluoromethylsulfonyloxy-7,8-dihydro-8,8-dimethylnaphth-2-yl)ethynyl]benzoate2×

Produkt 1

HCID 18314563Ethyl 4-[(7,8-dihydro-8,8-dimethyl-5-(1,1-dimethylethyl)naphth-2-yl)ethynyl]benzoate

Versuchsvorschrift

Employing the same general procedure as for the preparation of ethyl 4-[(7,8-dihydro-8,8-dimethyl-5-(1,1-dimethylethyl)naphth-3-yl)ethynyl]benzoate (Compound 71), 300 mg (0.63 mmol) of ethyl 4-[(5-trifluoromethylsulfonyloxy-7,8-dihydro-8,8-dimethylnaphth-2-yl)ethynyl]benzoate (Compound 87) was converted into the title compound (colorless oil) using 84 mg (0.94 mmol) of cuprous cyanide, 40 mg (0.94 mmol) of lithium chloride and 120 mg (1.1 ml, 1.88 mmol) of tert-butyllithium (1.7M solution in pentane).

Quellen und Nachweise

ORD-Eintrag
ord-ec3dee7ce9d84b6c8b673f6ab1329a9c
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05648514

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