ethyl pentanoate

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 100 milligram sample of the prepared hydroxy-ester is pyrolyzed in a sealed tube at 240°-245° C. for 1 hour. Examination of the pyrolyzate by liquid chromatography indicates that it consists of 60% of unreacted hydroxy-ester and 40% of a 1:1 mixture of ethyl valerate and benzaldehyde.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 10 milligram sample of the prepared hydroxy-ester is pyrolyzed in an open tube at 250° C. for 5 minutes. Examination of the pyrolyzate by G.C., L.C. and T.L.C. indicates >90% decomposition to form a 1:1 mixture of acetophenone and ethyl valerate. to form

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The procedure of Example 5 (i) was repeated except that vinyl valerate was used instead of 2,2,2-trichloroethyl butyrate to give 10.4 g of S-form of 1-(4-(tetrahydro-2-pyranyloxy)phenyl)ethanol (yield: 94%) and 13.9 g of R-form of 1-(4-tetrahydro-2-pyranyloxy)phenyl)ethyl valerate (yield: 91%).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A total of 9 Fernbach flasks, each containing 500 ml. broth, were sterilized for 30 minutes at 121° C. After cooling to room temperature, 5.0 ml. of sterile 50% dextrose solution and 5.0 ml of the 24 hour grown inoculum were added to each flask. The flasks were incubated at 30° C. at 100 rpm for 24 hours. Sterile 10% sodium cinnamate, pH 7.0, was added to each flask as follows, 5 g/l at 24 hours, 9 g/l at 48 hours, and 6 g/l at 72 hours. Samples of broth were analyzed periodically, by GC using ethyl pentanoate as an internal standard. After 44 hours of incubation, all the flasks were combined and product was extracted 3 times with ethyl acetate (approximately ½ volume each time). The combined extracts were washed 2 times with 100 ml. saturated NaHCO3 each time, followed by 2 times 100 ml saturated NaCl washes. The solvent was removed under vacuum and the crude extract was fractionally distilled to recover product. A yield of 2.7 g/L having a purity of 99.4% was obtained. were added to each flask The flasks were incubated at 30° C. at 100 rpm for 24 hours 5 g/l at 24 hours 9 g/l at 48 hours 6 g/l at 72 hours After 44 hours of incubation product was extracted 3 times with ethyl acetate (approximately ½ volume each time) The combined extracts were washed 2 times with 100 ml The solvent was removed under vacuum the crude extract was fractionally distilled to recover product was obtained

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A total of 9 Fernbach flasks, each containing 500 ml. broth, were sterilized for 30 minutes at 121° C. After cooling to room temperature, 5.0 ml. of sterile 50% dextrose solution and 5.0 ml of the 24 hour grown inoculum were added to each flask. The flasks were incubated at 30° C. at 100 rpm for 24 hours. Sterile 10% sodium cinnamate, pH 7.0, was added to each flask as follows, 5 g/l at 24 hours, 9 g/l at 48 hours, and 6 g/l at 72 hours. Samples of broth were analyzed periodically, by GC using ethyl pentanoate as an internal standard. After 44 hours of incubation, all the flasks were combined and product was extracted 3 times with ethyl acetate (approximately ½ volume each time). The combined extracts were washed 2 times with 100 ml. saturated NaHCO3 each time, followed by 2 times 100 ml saturated NaCl washes. The solvent was removed under vacuum and the crude extract was fractionally distilled to recover product. A yield of 2.7 g/L having a purity of 99.4% was obtained. were added to each flask The flasks were incubated at 30° C. at 100 rpm for 24 hours 5 g/l at 24 hours 9 g/l at 48 hours 6 g/l at 72 hours After 44 hours of incubation product was extracted 3 times with ethyl acetate (approximately ½ volume each time) The combined extracts were washed 2 times with 100 ml The solvent was removed under vacuum the crude extract was fractionally distilled to recover product was obtained

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: At room temperature, a mixture of pentanoic acid ethyl ester (0.4 mol) and diethyl oxalate (compound 11 in Scheme 1) (73.1 g, 0.5 mol) is added to a solution of NaOEt (32.7 g, 0.48 mol) in EtOH (250 ml). The mixture is stirred at room temperature for 30 minutes and EtOH is distilled away. The residue is then purified by vacuum distillation, which provides the product (120) as a clear oil. EtOH is distilled away The residue is then purified by vacuum distillation, which

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of 0.50 moles of propargylmagnesium bromide in 340 ml. of ether at -78° C. is added a solution of 65.2 g. (0.50 moles) of ethyl valerate in 100 ml. of ether during 60 minutes. The solution is stirred at -78° C. for 30 minutes and then hydrolyzed by pouring onto a mixture of ice and ether. The ether layer is washed with brine, treated with hydroquinone, dried over magnesium sulfate, and concentrated. The ether layer is washed with brine treated with hydroquinone dried over magnesium sulfate concentrated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Examples 351-356 in Table 19 were prepared in a similar multi-step manner as Example 300, step 1 wherein either ethyl pentanoate was converted to 4-chloro-2-methylsulfonyl-5-propylpyrimidine or ethyl hexanoate was converted to 5-butyl-4-chloro-2-methylsulfonylpyrimidine which were then each reacted with a) 3-methoxy-1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-one (described in Example 146, step 3), b) the title compound of Example 98, step 1, or c) 3-chloro-1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-one (described in Example 134) in a manner similar to Example 152, step 5 to give the title compound.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Examples 351-356 in Table 19 were prepared in a similar multi-step manner as Example 300, step 1 wherein either ethyl pentanoate was converted to 4-chloro-2-methylsulfonyl-5-propylpyrimidine or ethyl hexanoate was converted to 5-butyl-4-chloro-2-methylsulfonylpyrimidine which were then each reacted with a) 3-methoxy-1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-one (described in Example 146, step 3), b) the title compound of Example 98, step 1, or c) 3-chloro-1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-one (described in Example 134) in a manner similar to Example 152, step 5 to give the title compound.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 100 milligram sample of the prepared hydroxy-ester is pyrolyzed in a sealed tube at 240°-245° C. for 1 hour. Examination of the pyrolyzate by liquid chromatography indicates that it consists of 60% of unreacted hydroxy-ester and 40% of a 1:1 mixture of ethyl valerate and benzaldehyde.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 10 milligram sample of the prepared hydroxy-ester is pyrolyzed in an open tube at 250° C. for 5 minutes. Examination of the pyrolyzate by G.C., L.C. and T.L.C. indicates >90% decomposition to form a 1:1 mixture of acetophenone and ethyl valerate. to form