Ethyl naphthalene-1-carboxylate

Reactions of organomagnesium compounds with a,(3-unsaturated esters show a somewhat greater tendency to conjugate addition than reactions with a,p-unsaturated ketones (see p. 124). However, copper(i) catalysis may be beneficial even in cases where conjugate addition is the main uncatalysed reaction [30]  

For an example of conjugate addition of a Grignard reagent to a cyanoacrylate, see Section 5.3, p. 105. 

Carruthers, in Comprehensive Organometallic Chemistry (ed. G. Wilkinson), Ch. 49. Pergamon Press, Oxford, 1982. 

Posner, Org. Reactions 22, 253 (1975) G. H. Posner, An Introduction to Organic Synthesis Using Organocopper Reagents. Wiley, New York, 1980. 

Doring, E. Uhlig and L. Dahlenburg, Z. Anorg. Allg. Chem. 578,58 (1989) G. Cahiez and B. Laboue, Tetrahedron Lett. 33,4439 (1992). 

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Hydroxyzine pamoate is designated chemically as l-(p-chlorobenzhydryl)4-[2-(2-hydroxyethoxy) ethyl] diethyl-enediamine salt of l.l -methylene bis (2 hydroxyl-naphthalene carboxylic acid). Hydroxyzine pamoate 25 mg/5... 

Irradiation of complex 6 in the presence of ethyl acrylate provides the [6 + 2] 7t-adduct 9 as the single enrfo-diastereomer,276 which may also be obtained by heating a mixture of methyl l//-azepine-l-carboxylate with the ester in the presence of a catalytic amount of tricarbonyl(>]6-naphthalene)chromium(O).277... 

This type of reaction was originally carried out with ethyl iodide1 and has been extended to other alkyl halides,2 halogeno-carboxylic esters3 and to substituted arsine halides.4 Incidentally when p-toluene sulphonyl chloride and naphthalene-2-sulphonyl chloride were allowed to react with sodium diethyl phosphite, the corresponding disulphones were obtained in small yield.5... 

Esters of 2-(2-azidophenyl)ethyl alcohol are photolyzed under a high-pressure mercury lamp to a reactive nitrene intermediate which, following insertion into the alkyl side-chain, undergoes elimination to give the free carboxylic acid (up to 32%) and producing indole. The photochemical release was somewhat improved (65-80%) when 5-azido-4-(hydroxy-methyl)-l-methoxy naphthalene was used (see Scheme 27). 

CPCCOEt, selective mGluRI antagonist, 2-Hydroxyimino-1a,2-dihydro-1W-7-oxa-cyclopropa[b]naphthalene-7a-carboxylic acid ethyl ester... 

Jew and Park achieved a highly enantioselective synthesis of (2S)-a-(hydroxy-methyljglutamic acid, a potent metabotropic receptor ligand, through the Michael addition of 2-naphthalen-l-yl-2-oxazoline-4-carboxylic acid tert-butyl ester 72 to ethyl acrylate under phase-transfer conditions [38]. As shown in Scheme 5.36, the use of BEMP as a base at —60 °C with the catalysis of N-spiro chiral quaternary ammonium bromide le appeared to be essential for attaining an excellent selectivity. 

Pravastatin was isolated as products of enzymatic hydroxylation by some kinds of microorganisms of [lS-[l-a(R ),7p,8P(2S, 4S )8a 3]]-2-methylbutanoic acid l,2,3,7,8,8a-hexahydro-7-methyl-8-[2-(tetrahydro-4-hydroxy-6-oxo-2))-pyran-2-yl)ethyl]-l-naphthalenic lactone (campactin) or their carboxylic acid or their salts (products of animal metabolism of microorganisms from the genera Nocardia, Streptomyces et cetera). 

In a third microreactor, the anion of 4-ferf-butyl l-ethyl-2-(diethox-yphosphoryl)succinate was prepared in situ using sodium ethoxide 237 (in EtOH) and the Wittig-Horner olefination with benzaldehyde 116 performed using a residence time of 47 min to afford (E)-ferf-butyl-l-ethyl-2-benzylidenesuccinate 238 in excellent selectivity (89% yield). In a fourth reactor, the acid-catalyzed (TFA 239) ferf-butyl ester deprotection was achieved using a residence time of 5 min at 34 °C and employing DCM as the reaction solvent to afford (E)-3-(ethoxycarbonyl)-4-phenylbut-3-enoic acid 246 in 82% yield. The deprotection was subsequently followed by a Friedel-Crafts acylation, using triethylamine 14 and acetic anhydride 37, to afford 4-acetoxy-naphthalene-2-carboxylic acid ethyl ester 241 in quantitative yield when conducted at 130 °C (residence time = 47 min). 

A solution of this ester (8.35 g, 21.6 mmol, 1.0 equivalents) in tetrahydrofuran (THF 100 mL) was cooled to 0 °C, and pyridinium p-toluenesulfonate (PPTS, 500 mg, 2.00 mmol, 0.1 equivalents) and then 2,2-dimethoxypropane (20.0 mL, 163 mmol, 5.9 equivalents) were added. The cold bath was removed and the mixture was stirred at room temperature for 48 h, quenched with saturated aqueous NaHCOs solution, and extracted with EtOAc. The combined organic layers were washed with brine, dried (Na2SO4), filtered, and concentrated. Purification by chromatography on SiO2 (3% ethyl acetate and 1% triethylamine in hexanes, and then 100% EtOAc) afforded the acetonide and a small amount of starting diol which was re-subjected and purified as above. The two batches were combined to afford naphthalene-2-carboxylic acid 2-[(4S)-2,2- dimethyl-[l,3]dioxan-4-yl]-2-methylpropyl ester (9.140 g, 97%) as a clear colorless syrup. Reference Wipf, P Graham, T. H.,/. Am. Chem. Soc. 2004,126, 15346-15347. 

Ott D, Floersheim P, Inderbitzin W et al (2000) Chiral resolution, pharmacological characterization, and receptor docking of the noncompetitive mGlul receptor antagonist (+/-)-2-hydroxyimino- la, 2-dihydro-lH-7-oxacyclopropa[b]naphthalene-7a-carboxylic acid ethyl ester. J Med Chem 43 4428-4436... 

Z)-Ethyl 3-(naphthalen-l-ylmethyl)-2-(2-oxo-2-phenylethylidene)-2,3-dihydrothiazole-4-carboxylate (5c) Yield 75%... 

Periasamy et at. obtained aldehydes in good yield from poly-cyclic aromatic hydrocarbon radical anions prepared by the addition of sodium to the aromatic hydrocarbon in THF, followed by formylation with carboxylic acid esters or N,N-dialkyformamides. Reactions of sodium naphthalenide, -anthracenide and -phenan-threnide with ethyl formate yielded the corresponding aldehydes. Substituted naphthalenes e.g. acenaphthene and 2-methylnaphthalene are also formylated using A/,A/-dialkylformamides, but in low yields (20% and 26% respectively). 

Liu et al., reported the synthesis of ethyl 5-(2,6-dichlorophenyl)-7-methyl-2-(1 -naphthylmethylene)-3 -oxo-2,3 -dihydro-5H-thiazolo[3,2-a]pyrimidine-6-carboxylate 37 (Scheme 15). The reaction of ethyl 2-mercapto-4-methyl-6-(2,6-dichlorophenyl)-l,6-dihydro-pyrimidine-5-carboxylate, ethyl chloroacetate and naphaldehyde in acetic acid and acetic anhydride afforded the target molecule 37. In the molecular, the thiazolo[3,2-a]pyrimidine and naphthalene systems are essentially coplanar, with a dihedral angle between the combined plane and the mean plane of the benzene ring of the 2,6-dichlorophenyl substituent of 94.7(4)° [39]. 

C13H12O2 naphthalene-l-carboxylic acid ethyl ester 3007-97-4... 

C13H12O2 naphthalene-2-carboxylic acid ethyl ester 3007-91-8... 

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