Ethyl sorbate

Diethyl azodicarboxylate forms normal adducts with 2,3-dimethylbutadiene and with ethyl sorbate however, it is not a very good dienophile, presumably because it exists in the fraws-configuration. The sterically hindered diene 254 adds the ester to give mainly the ene product 255 (equation 137) and even cyclohexa-1,3-diene undergoes an analogous... 

Early investigations of additions of soft carbon nucleophiles to simple Michael acceptors like ethyl sorbate date back to the beginning of the 20th century. Already in 1906, Vorlander and coworkers4-6 described additions of malonate anion whereas ethyl sorbate provided the 1,6-addition product6 (equation 2), the 1,4-adduct was obtained from methyl 5-phenyl-2,4-pentadienoate4 (equation 3). Thus, it seems that the regioselectivity... 

An understanding of olefin chemoselectivity in CM is also crucial when homologating 1,3-dienes, which represent a particularly challenging substrate class. In 2005, Grubbs and co-workers demonstrated that, by employing either an electronic or steric barrier to reaction, one of the olefins in a conjugated diene could be deactivated relative to the other for CM. For example, in the reaction of ethyl sorbate with 5-hexenyl acetate in the presence of 5 (I0mol%),... 

Starting from commercially available ethyl sorbate (64) dihydroxylation with standard AD-mixes afforded diol 65 with 80% ee in 61% chemical yield [94). Protection as the acetonide followed by ozonolysis led to the formation of key intermediate 66 in a four step sequence from diol 65 in 33% overall yield. Further transformations gave fluoroglycoside 67, which was then used in a stereoselective glycosylation. 

The configuration of the adduct 8, obtained from ethyl sorbate and diethyl diazenedicarboxy-late, has not been established24, but the ci.v-isomer would be the expected product if the reaction proceeds via a concerted [4 + 2] cycloaddition. 

For ell ecling addition of the ethoxyethynyl group to the carbonyl group of cro-tonaldehyde. Stork and Tomasz added ethoxyacetylene in ether to an ethereal solution of phenylUthium and added the aldehyde to the resulting suspension of lithium ethoxyacetylide (1). The resulting carbinol is rearranged readily under acid catalysis to ethyl sorbate (4). 

Finally, a high regioselectivity has been observed in the chlorine addition to ethyl sorbate (20) in methanol (equation 31). Under ionic conditions the reaction gives mainly products arising from addition to the y—S bond and the solvent opens the corresponding ionic intermediate preferably at the allylic carbon to give product 21. A bridged structure... 

Of our two approaches, the iterative asymmetric dihydroxylation of dienoates (Scheme 1) is the most efficient in terms of steps (1 to 3 steps). For instance, dienoates, like ethyl sorbate (1.1 R = CH3), react under the Upjohn conditions (OSO4/NMO) 14) o give racemic y-ga/ac/o o-lactones in only one... 

Enamines undergo [4 + 2]cycloaddition with electrophilic alkenes such as ethyl sorbate, methyl 2,4-pentadienoate , penta-2,4-dienol , hexa-3,5-dien-2-... 

COOC2H5)2 + CH3CH=CHCOOC2H5 — C2H5OOCCOCH2CH=CHCOOC2H5 The similar condensation of ethyl sorbate is detailed below as an example of the procedure 758... 

Diethyl 7-oxo-2,4-octadienedioate Potassium (13 g), under ether (85 ml), is treated with ethanol (58 ml). Then a mixture of diethyl oxalete (24.3 g) and ether (10 ml) is added with cooling in ice and shaking, followed 15 min later by a mixture of ethyl sorbate (23.3 g) and ether (10 ml), whereupon the mixture at once becomes deep red. The flask is then securely stoppered and set aside for 24 h, after which the potassium enolate that has separated is filtered off as fast as possible, washed with cold water, and dried on porous plate in a desiccator. This enolate (27-28 g) is dissolved in water, and the solution is acidified with 2N-acetic acid the precipitated free ester soon solidifies and after recrystallization from ethyl acetate or light petroleum melts at 100°. 

Ethyl /rans,/rans-2,4-hexadlenoate Ethyl sorbate C9FI-12O2 2396-84-1 140.180 196.6 0.9606 9 1.4961 9 vs eth, EtOH, chi... 

Commercially available ethyl sorbate was easily converted into chiral diol by Sharpless asymmetric dihydroxylation and by subsequent selective silylation into allyl alcohol 120. This intermediate was transformed into... 

A solution of 15 g tosylmethyl isocyanide (75 mmol) and 10.0 g ethyl sorbate (71.3 mmol) in 50 mL dry DMSO and 100 mL ether was added to an ice cold suspension of 3.6 g NaH (88.5 mmol, 59% dispersion in oil) in 100 mL ether. The mixture was stirred for 3 h at 20°C, poured into 50 mL saturated aqueous NH4CI solution, and extracted with ether (4 x 50 mL). The combined extracts were washed with saturated aqueous NH4CI solution, and dried over MgS04. Evaporation of the extract gave 13.0 g of crude ethyl 3-(4-methyl-3-pyrrolyl)acrylate. Crystallization from EtOH gave 10.6 g of pure product, in a yield of 80% m.p. 88-89°C. 

See Cetethyidimonium bromide Ethyl-N-hexadecylmorpholinium ethosulfate Ethyl-4-hexadecylmorpholinium ethyl sulfate. See Cetethyl morpholinium ethosulfate Ethyl-2,4-hexadienoate. See Ethyl sorbate Ethylhexaldehyde 2-Ethylhexaldehyde Ethyl hexanal. See 2-Ethylhexanal 2-Ethylhexanal... 

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