Ethyl 3-methylpentanoate

Ethyl 2-Hydroxypropionate, 72 Ethyl Lactate, 72 Ethyl Levulinate, 72 Ethyl 2-Methylbutyrate, 72 Ethyl 2-Methylpentanoate, 74 Ethyl 3-Methylthiopropionate, 74 Ethyl 3-Oxybutanoate, 72 Ethyl ra-Pentanoate, 74 Ethyl Salicylate, 74 Ethyl 10-Undecenoate, 74 Ethyl Valerate, 74... 

AI3-33618 EINECS 254-384-1 Ethyl 2-methylpentanoate Ethyl 2-methyivalerate Ethyl a-methylvalerate FEMA No. 3488 Pentanoic acid, 2-methyl-, ethyl ester. Oil with a natural, fruity, pineapple odor. Used in specialty perfumes and fruit flavorings. Oil bpi5 = 60" d n 0.861-0.865. Quest Inti. 

Ethyl 2-methylpentanoate. See Ethyl 2-methylvalerate Ethyl methylphenylglycidate CAS 77-83-8 EINECS/ELINCS 201-061-8... 

Synonyms Ethyl 2-methylpentanoate 2-Methylvaleric acid ethyl ester Pentanoic acid, 2-methyl-, ethyl ester... 

Heating the reaction for shorter periods gave erratic results. At this point the semisolid mixture can be diluted with 200 ml. of water, extracted with benzene, and the benzene extract fractionally distilled to give ethyl 2,3-dicyano-3-methylpentanoate, b.p. 146.0-147.5° (2.5 mm.), m27d 1.4429 (highly purified ester has b.p. 138.5-141.5° (2 mm.), 25d 1.4432). The overall yield of a-ethyl-a-methylsuccinic acid is decreased by about 5% when the dicyano intermediate is isolated. 

B. Ethyl 3-benzyl-2-cyano-3-methylpentanoate. A 2-1. threenecked round-bottomed flask, fitted with a tantalum wire Hersh-berg stirrer, a condenser, and a separatory funnel, is arranged for use of a nitrogen atmosphere.2 Magnesium (19.2 g., 0.79 g.-atom) and 100 ml. of dry ether 3 are placed in the flask, and a solution of 100 g. (91 ml., 0.79 mole) of benzyl chloride in 500 ml. of dry ether is added in a period of 1.5-2.0 hours, with stirring, while the mixture boils spontaneously. The mixture is koiled for 15 minutes after completion of the addition, then a solution of 110 g. (0.66 mole) of ethyl sec-butylidenecyanoacetate in 130 ml. of benzene is added over a 30-minute period with spontaneous reflux. The reaction mixture is stirred and heated under rellux for an additional hour. A precipitate separates after about 30 minutes. 

The ethyl 3-benzyl-2-cyano-3-methylpentanoate, 3-benzyl-3-methylpentanenitrile, and 3-benzyl-3-methylpentanoic acid preparations follow the procedure given by Prout, Huang, Hartman, and Korpics.9... 

Applying these rules gives the following compound the name 2-ethyl-4-methylpentanoic acid. 

Dibenzyl malonate (124.5 g, 0.44 mol) was taken up in dry DMF and potassium t-butoxide (49.2 g, 0.44 mol) was added portionwise with stirring and cooling. When a homogeneous solution had formed it was cooled to 0°C, then t-butyl-2R-bromo-5-methylpentanoate (110.1 g, 0.44 mol) in DMF (200 ml) was added dropwise over 1 h. When addition was complete the reaction was transfered to a cold room at 5°C and left for 4 days. The reaction mixture was partitioned between ethyl acetate and saturated ammonium chloride then the aqueous layer extracted with further ethyl acetate (4 x 500 ml), drying and solvent removal left an oil (228.0 g) heavily contaminated with DMF. This oil was taken into ether (1 L) and washed with brine (2 x 11) then the organic layer dried (magnesium sulfate), solvent removed under reduced pressure to leave the benzyl (2-benzyloxycarbonyl-3R-(t-butoxycarbonyl)-5-methylhexanoate (179.0 g) contaminated with a small amount of dibenzyl malonate. 

Campo, E., Cacho, J., and Eerreira, V. (2006a). Multidimensional chromatographic approach applied to the identification of novel aroma compounds in wine - Identification of ethyl cyclohexanoate, ethyl 2-hydroxy-3-methylbutyrate and ethyl 2-hydroxy-4-methylpentanoate. 

Probkm 28.28 Using 9-BBN plus any alkenes and unhalogenated acids or ketones, outline all steps in the synthesis of (a) 2-heptanone (b) 4-methylpentanoic acid (c) 4-methyl-2-hexanone (d) l-cyclohexyl-2-propanone (e) ethyl (trans Z-methylcyclopentyl)acetate (f) l>phenyl-4-methyM-pentanone (g) i-cyclopentyl-33 dimethyl-2-butaBone. 

Trialkylsiloxybutyrate, 267 4-Acetoxy-2,2-dimethylbutyrate, 267 2,2-Dimethyl-4-pentenoate, 267 2-Iodobenzoate, 267 4-Nitro-4-methylpentanoate, 268 o-(Dibromomethyl)benzoate, 268 2-Formylbenzenesulfonate, 268 4- (Methylthiomethoxy) butyrate, 268 2- (Methylthiomethoxymethyl) benzoate, 269 2- (Chloroacetoxymethyl) benzoate, 269 2- [(2-Chloroacetoxy) ethyl] benzoate, 269 2- [2- (Benzyloxy)ethyl]benzoate, 269 2- [2- (4-Methoxybenzyloxy)ethyl[ benzoate, 269... 

Longer chained 2-oxo alkanoates, as well as 4-methyl-2-oxopentanoates, behave in a similar manner (Table 4). e.g., ethyl 4-methyl-2-oxopentanoate gives ethyl (S )-2-hydroxy-4-methylpentanoate with 75% ee upon reduction with Alpine-Borane29. 

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