4.7- dimethoxy-2-ethyl

SYNTHESIS To a solution of 19.7 g 2,5-dimethoxy-4-ethylbenzaldehyde (see the recipe for 2C-E for its preparation) in 72 g glacial acetic acid there was added 6.5 g anhydrous ammonium acetate and 10.2gnitroethane. After heating for 1.75hon the steam bath, the reaction mixture was cooled in a wet ice bath, diluted with 10 mL H20, and seeded with a small crystal of product. The yellow crystals were removed by filtration (7.6 g wet with acetic acid) and another 2.25 g was obtained from the mother liquors with additional H20. The combined fractions were recrystallized from 25 mL boiling MeOH, to give 6.5 g fine yellow crystals of l-(2,5-dimethoxy-4-ethyl)-2-nitropropene, with a mp of67.5-68.5 °C. Anal. (C1(Hi N04) C,H,N. 

Benzaldehyd 2,5-Dimethoxy-4-ethyl-E3, 24 (H - CHO) Benzocyclobutene 1,1,6-Trimethoxy-E17f, 976 [1-Br— 1-OR— benzene... 

Snyder, S. H., Weingartner, H. and Faillace, L. A. (1970) DOET (2,5-Dimethoxy-4-ethyl-amphetamine) and DOM (2,5-Dimethoxy-4-methylamphetamine), new psychotropic agents. Their effects in man. In Psychotomimetic Drugs, D. H. Efron (Ed), Raven Press, New York, pp. 247-264. 

A total of 120 mL of 1.0 M solution of LAH in THF (120 mL of 1.0 M) was transferred to a 3 neck 500 mL flask, under an inert atmosphere with good magnetic stirring. This solution was cooled to deg C with an external ice-water bath, and there was then added 3.0 mL of 100% H2S04 over the course of 0.5 h. This was followed by a solution of 5.85 g of 2,5-dimethoxy-4-ethyl-beta-nitrostyrene, in 40 mL of warm THF. The reaction mixture was stirred for 0.5 h, brought to room temperature, heated on the steam bath for 0.5 h, and then returned to room temperature. The addition of IPA dropwise destroyed the excess hydride, and some 4.5 mL of 5% NaOH produce a white cottage cheese, in a basic organic medium. This mixture was filtered, washed with THF, and the filtrate evaporated to produce 2.8 g of an almost white oil. 

Di-(2-imidazolyl)-nitro-methan wird zu 97% durch Erhitzen von 4,6-Bis-[2,2-dimethoxy-ethyl-amino]-5-mtro-pynmidm in konz. Salzsaure erhalien434 ... 

Hexene 4-(2,2-Dimethoxy-ethyl-seleno)-3-fluoro- ElOb,. 380 (In + XcF2 R —Sc—Sc— R)... 

Hydrocinnamic acid, a-acetyl-2,3-dimethoxy-, ethyl ester)... 

Triazen 3-(2,2-Dimethoxy-ethyl)-l-(4 nitro-phenyl)- E16a, 1189 (Ar-Nf + Amin)... 

Tellurium (2,2-Dimethoxy-ethyl)-phenyl- E12b, 389 (Ar2Te2 +... 

Cyclopropan l,l-Dichlor-3-(2,2-dimethoxy-ethyl)-2-(dimethoxy-methyl)- E17a, 653 (CHCI3/ NaOH + En)... 

Pyrrol l-(2,2-Dimethoxy-ethyl)-5-methoxycarbonyl-2-methyl- E6a, 591 [H3C-CO-(CH2)2-CO-COOR + H2N-CH2-CH(OR)2]... 

Azetidin ci.v/tr[Pg.1082]

DIMETHOXY ETHYL PHTHALATE see DOF400 DI(2-METHOXYETHYL)PHTHALATE see DOF400 DIMETHOXYMETHANE see MGA850 DIMETHOXYMETHYLBENZENE see DOG700 DIMETHOXYMETHYLSILANE see MJE900... 

DAOS = 3,5-dimethoxy- -ethyl- -(2-hydroxy-3-sulfopropyl)-aniline sodium salt... 

DIMETHOXY-, ETHYL ESTER, 31,56 2-CARBOXY-, 34, 8 Hydrogenation, of a double bond,... 

Ethyl/4-Methyl 2-(l, 1 -Dimethoxy-ethyl)-3-ethyl- 2133 C,3H24PPd Benzopalladet... 

Dimethoxy-ethyl)-cyclo-pentylj-ethenyl - -trimethyl-silyloxy- 2424... 

Diisopropyl- 2432 2-(2,2-Dimethoxy-ethyl)- 2432 2-(Dimethoxy-methyl)-methyl- 2433 2-(Dimethoxy-methyl>2-phenyl- 2433... 

Methyl-l-nitroso urea was subsequently shown to be a potent carcinogen (see Sect. 4.2), and its use is now discouraged. For the synthesis of diazoalkanes, for which no other route is described in the literature, N-alkyl-N-nitroso ureas may still be the reagent of choice. This is the case, for example, for diazo acetaldehyde (2.48), which was obtained (2-18) by Abdallah et al. (1983) by cleavage of A-(2,2-dimethoxy-ethyl)-AT-nitroso urea (2.47). The corresponding iV-nitroso urea was also used successfully for the preparation of 4-(2-diazoethyl)-2,3,3-trimethylcyclopentene (2.49) by Adam et al. (1985). Various other methods failed to lead to this diazoalkane. 

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