Sodium methoxide, hydrogenation with

The 2 -deoxythioguanosine 13 is prepared from 2-acetamido-6-chloro-9-[2-deoxy-3,5-di-d)-(4-toluoyl)-/ -D-ribofuranosyl]purine by replacement of the chlorine and removal of the toluoyl groups in one step with methanolic sodium methoxide saturated with hydrogen sulfide. ... 

Methanol reacts with sodium metal to give sodium methoxide along with the evolution of hydrogen gas. 

Isatin (190) is a compound with interesting chemistry. It can be iV-acetylated with acetic anhydride, iV-methylated via its sodium or potassium salt and O-methylated via its silver salt. Oxidation of isatins with hydrogen peroxide in methanolic sodium methoxide yields methyl anthranilates (81AG(E)882>. In moist air, O-methylisatin (191) forms methylisatoid (192). Isatin forms normal carbonyl derivatives (193) with ketonic reagents such as hydroxylamine and phenylhydrazine and the reactive 3-carbonyl group also undergoes aldol condensation with active methylene compounds. Isatin forms a complex derivative, isamic acid (194), with ammonia (76JCS(P1)2004). 

Methyldihydrostrychnidinium-A acetate is produced in much small amount in the hydrogenation ( internal alkylation) reaction and w isolated as the iodide, m.p. 345-350°, and converted to the chloric which on treatment with sodium methoxide gave methoxymethyltetr hydrostrychnidine (c in the above list) with some des-base-D, and < thermal decomposition yielded dihydrostrychnidine-A. These and oth reactions of des-base-D are regarded as best accounted for by formu (XVIII). ... 

Difluorododecane is unaffected by sodium methoxide in methanol, but its treatment with potassium tert-butoxide in tetrahydrofuran eliminates hydrogen fluonde stereospecifically rneso and dl compounds give, respectively, ( )- and (2) 6 fluoro 6 dodecene [12] (equation 11)... 

Shaw and McDowellhave prepared imidazolone derivatives by cyclization of a-acylamino amides. In a variation of this reaction the azlactone (30) was gradually converted to the hydroxamic acid (31) by methanolic hydroxylamine. Sodium methoxide and hydroxylamine readily gave the acyclic hydroxamic acid (32) which could be cyclized to 31 by dilute acid. Benzyloxyurea has been used in the sjrnthesis of pyrimidine hydroxamic acids (33) by reaction with /S-diketones followed by catalytic hydrogenation of the benzyl group. Protection... 

Sodium methoxide (1.2 g) in dimethylformamide (150 ml) was stirred with 3,5-dim ethoxy-4 reaction mixture was then treated with /3-morpholinoethyl chloride (3.4 g) and heated for 1 hour at 140°C, then evaporated to dryness, and treated with water to give a solid material. The mixture was filtered, washed and crystallized from cyclohexane to give 3,5-di-methoxv-4 -chloro-4-( morpholinoethoxy)-benzophenone (6.5 g), MP 91°C to 92°C. The product was then reacted at about 0°C with gaseous hydrogen chloride in ether to give, after crystallization from isopropanol, the corresponding hydrochloride which hada MPof 187.9°C. 

Deoxy-D-jcylo hexose 6-(dihydrogen phosphate) (21) has also been synthesized (2) the reaction sequence makes use of 3-deoxy l 2,5 6-di-O-isopropylidene D-galactofuranose (16), a compound that can be easily prepared from D-glucose (2, 60). The mono-isopropylidene derivative (17) formed by partial hydrolysis of the di-ketal is converted into the 6-tosylate (18) by reaction with one molar equivalent of p-toluenesulfonyl chloride. From this the epoxide (19) is formed by reaction with sodium methoxide. Treatment of the anhydro sugar with an aqueous solution of disodium hydrogen phosphate (26) leads to the 6-phosphate (20)... 

Treatment of the (bromoalkyl)-l//-2-benzazepine 24 (see Section 3.2.1.1.1.1.) with sodium methoxide results in attack by methoxide ion at position C5 of the C5-C6 double bond followed by loss of hydrogen bromide and formation of the cyclopropano derivative 25.80... 

If 4-azidoquinolines with substituents such as a carbonyl group in position 2 or 8 are irradiated in the presence of sodium methoxide the resulting 1//-benzodiazepines 3 are stabilized by hydrogen bonding between the ring NH and a neighboring 2- or 9-acyl carbonyl group and are readily isolated.216,217... 

Streitweiser et al.597 have also measured second-order rate coefficients for hydrogen exchange of fluorobenzenes with sodium methoxide in methanol, Table 182. Nucleophilic displacement of fluoride ion by methoxide ion accompanies... 

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