Benzoate → Ethyl 4-[(7,8-dihydro-5,8,8-trimethylnaphth-3-yl)ethynyl]benzoate

HRID 277529Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 277529
C([O-])(=O)C1C=CC=CC=1.[CH3:10][C:11]1([CH3:38])[C:20]2[CH:19]=[CH:18][C:17]([C:21]#[C:22][C:23]3[CH:33]=[CH:32][C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:25][CH:24]=3)=[CH:16][C:15]=2[C:14]([C:34](C)(C)C)=[CH:13][CH2:12]1.FC(F)(F)S(OC1C2C=C(C#CC3C=CC(C(OCC)=O)=CC=3)C=CC=2C(C)(C)CC=1)(=O)=O>>[CH3:34][C:14]1[C:15]2[CH:16]=[C:17]([C:21]#[C:22][C:23]3[CH:33]=[CH:32][C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:25][CH:24]=3)[CH:18]=[CH:19][C:20]=2[C:11]([CH3:10])([CH3:38])[CH2:12][CH:13]=1

Komponenten

4

Edukt 3

HCID 242BenzoateHCID 120176384-[2-[5,6-Dihydro-5,5-dimethyl-8-[[(trifluoromethyl)sulfonyl]oxy]-2-naphthalenyl]ethynyl]benzoic acid ethyl ester2×HCID 18314564Ethyl 4-[(7,8-dihydro-8,8-dimethyl-5-(1,1-dimethylethyl)naphth-3-yl)ethynyl]benzoate

Produkt 1

HCID 18314561Ethyl 4-[(7,8-dihydro-5,8,8-trimethylnaphth-3-yl)ethynyl]benzoateAusbeute 0,5 %

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), 250 mg (0.52 mmol) of ethyl 4-[(5-trifluoromethylsulfonyloxy-7,8-dihydro-8,8-dimethylnaphth-3-yl)ethynyl]benzoate (Compound 66) was converted into the title compound (HPLC Partisil 10, 0.5% EtOAC-hexanes) using 70.2 mg (0.78 mmol) of cuprous cyanide, 33.2 mg (0.78 mmol) of lithium chloride and 34.5 mg (1.28 ml, 1.57 mmol) of methyllithium (1.22M solution in Et2O).

Quellen und Nachweise

ORD-Eintrag
ord-6379556505b04ff39913b2110ef873eb
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06355806B1

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