Ethyl 2-methyl-2-hydroxypropanoate,

Ethyl Lactate Hydroxypropanoic Acid, Ethyl Ester Methyl Methacrylate... 

These reductions follow a similar procedure as for 1-phenylethanone at atmospheric pressure (vide supra). However, they are generally complete in 4 hours at 25 C or 24 hours at 0 °C, except in the case of methyl 3-mcthyl-2-oxobutanoatc which requires 8 days at 25 °C. Slightly better asymmetric inductions may be achieved using boranes with larger steric requirements12, e.g., the reduction of methyl 2-oxopropanoate with the 2-ethyl analog of Alpine-Borane yields methyl (5)-2-hydroxypropanoate with 97 % ee. 

Methyl ethyl carbinol. See 2-Butanol Methylethylcetoxime. See Methyl ethyl ketoxime 1-Methyl ethylene carbonate. See Propylene carbonate Methyl ethylene glycol. See Propylene glycol Methyl ethylene oxide. See Propylene oxide Methyl ethyl glycol. See Propylene glycol 1-Methylethyl hexandecanoate. See Isopropyl palmitate 1-Methylethyl 2-hydroxypropanoate. See Isopropyl lactate 4,4 -(1-Methylethylidene) biscyclohexanol. See Bisphenol A, hydrogenated 4,4 -(1-Methylethylidene) bisphenol. See Bisphenol A 2,2 -((1-Methylethylidene) bis (4,1-phenyleneoxymethylene)) bisoxirane. See Bisphenol A diglycidyl ether... 

Scheme 9.33. The formation of a diasteromer of a 2-(l-methyl-l-phenyl)ethyl-4-methylcy-clohexyl 3-(l-cyclohexenyl)-2-hydroxypropanoate from tin(IV) chloride catalyzed ene reaction between methylenecyclohexane and the corresponding glyoxalate ester.

Examples 1 to 5 in Table 1.1 illustrate simple displacement of a bromide (reactions 1 and 4) or a chloride (reactions 2,3, and 5). Reaction 1 illustrates a radical chain extension reaction that reacts ethylene and methyl bromoacetate 1.17), with AIBN (flzofeis-isobutyronitrile) as a catalyst, to produce the requisite bromo-cster. The reaction is not very selective, however, since it produced a mixture of 1.18 and 1.19. The reaction was not very selective and the observed products arose from addition of one and two equivalents of ethylene, respectively, to 1.17. Subsequent treatment with ammonia, the key reaction for this section, led to a mixture of 4-aminobutanoic acid and 6-aminohexanoic acid, 1.2 and 1.4. In reaction 2, ethyl 4,4,4-trifluoropropanoate (J.20) reacted with PCI3 and bromine to give ethyl 3-bromo-4,4,4-trifluorobutanoate, which reacted with ammonia to give 3-amino-4,4,4-trifluorobutanamide, 1.21. Reaction 3 shows the reaction of P-halo lactic acid (3-chloro-2-hydroxypropanoic acid, 1.22) with 28% aqueous ammonia, in an autoclave, to give isoserine (3-amino-2-hydroxypropanoic acid, 1.23). Both halo-acids l and halo-esters 2 have been converted into hydroxy amino acids typical products are 3-... 

C4H8O3 + C4H8O3 + C5H10O3 + Ethane-1,2-diol ethanoate + Methyl (S)-(-)-2-hydroxypropanoate + Ethyl (S)-(-)-2-hydroxypropanoate EVLM nil EVLM nil EVLM 1131 LB5271 LB2248 LB3943... 

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