ethyl 2-hydroxyhexanoate

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

Procedure: Imidazole (4.10 g, 60.22 mmol) and TBDMSCl (3.60 g, 23.89 mmol) was added to a stirred solution of 2-hydroxy-hexanoic acid ethyl ester (3.20 g, 19.97 mmol) in DMF (25 mL). The reaction mixture was kept at ambient temperature for 18 hrs. Water and diethyl ether were added and the two phases were separated. The aqueous phase was extracted with diethyl ether. The organic extracts were combined and washed sequentially with 0.5 M HCl and water, dried over MgSO4 and concentrated in vacuo to give the title product (5.30 g), 1H NMR (300 MHz, CDCl3) δ 4.18 (m, 3H), 1.69 (m, 2H), 1.35 (m, 4H), 1.28 (t, 3H), 0.91 (m, 12H), 0.07 (d, 6H). the two phases were separated The aqueous phase was extracted with diethyl ether washed sequentially with 0.5 M HCl and water dried over MgSO4 concentrated in vacuo

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

Procedure: Imidazole (4.10 g, 60.22 mmol) and TBDMSCl (3.60 g, 23.89 mmol) was added to a stirred solution of 2-hydroxy-hexanoic acid ethyl ester (3.20 g, 19.97 mmol) in DMF (25 mL). The reaction mixture was kept at ambient temperature for 18 hrs. Water and diethyl ether were added and the two phases were separated. The aqueous phase was extracted with diethyl ether. The organic extracts were combined and washed sequentially with 0.5 M HCl and water, dried over MgSO4 and concentrated in vacuo to give the title product (5.30 g), 1H NMR (300 MHz, CDCl3) δ 4.18 (m, 3H), 1.69 (m, 2H), 1.35 (m, 4H), 1.28 (t, 3H), 0.91 (m, 12H), 0.07 (d, 6H). the two phases were separated The aqueous phase was extracted with diethyl ether washed sequentially with 0.5 M HCl and water dried over MgSO4 concentrated in vacuo

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

Procedure: In a three-neck flask, at 20° C. and under an inert atmosphere, are mixed ethyl 2-hydroxycaproate (24.24 g; 150 mmol) and sodium methylate in solution in methanol (25% w/w) (1.6 g; 7 mmol). To this mixture, is added dimethylamine in solution in methanol (50% w/w) (26.75 g; 297 mmol) within 30 minutes. The temperature of this mixture is brought to 40° C. and maintained for 3 hours. After the return of the temperature of this reaction mixture to 20° C., orthophosphoric acid is added until a pH of 5 is obtained. The salts formed are removed by filtration and the solvents are removed under reduced pressure. 2-hydroxy-N,N-dimethylhexanamide is then obtained with a purity of 98%, i.e. a yield of 81%. is brought to 40° C. maintained for 3 hours is obtained The salts formed are removed by filtration the solvents are removed under reduced pressure

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

Procedure: In a three-neck flask, at 20° C. and under an inert atmosphere, are mixed ethyl 2-hydroxycaproate (24.24 g; 150 mmol) and sodium methylate in solution in methanol (25% w/w) (1.6 g; 7 mmol). To this mixture, is added dimethylamine in solution in methanol (50% w/w) (26.75 g; 297 mmol) within 30 minutes. The temperature of this mixture is brought to 40° C. and maintained for 3 hours. After the return of the temperature of this reaction mixture to 20° C., orthophosphoric acid is added until a pH of 5 is obtained. The salts formed are removed by filtration and the solvents are removed under reduced pressure. 2-hydroxy-N,N-dimethylhexanamide is then obtained with a purity of 98%, i.e. a yield of 81%. is brought to 40° C. maintained for 3 hours is obtained The salts formed are removed by filtration the solvents are removed under reduced pressure

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

Procedure: The title compound was prepared from 4′-(2-benzyl-benzofuran-3-yl)-3,5-dibromo-biphenyl-4-ol, and ethyl DL-2-hydroxycaproate, in substantially the same manner, as described in Example 1, steps g-h , and was obtained as a white solid, mp 75-76° C.; MS m/e 645 (M−H)+; was obtained as a white solid, mp 75-76° C.

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

Procedure: The title compound was prepared from 4′-(2-benzyl-benzofuran-3-yl)-3,5-dibromo-biphenyl-4-ol, and ethyl DL-2-hydroxycaproate, in substantially the same manner, as described in Example 1, steps g-h , and was obtained as a white solid, mp 75-76° C.; MS m/e 645 (M−H)+; was obtained as a white solid, mp 75-76° C.

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

Procedure: Ethyl 2-((tert-butyldimethylsilyl)oxy)hexanoate 5 (2.54 g) was prepared in 74% yield using ethyl 2-hydroxyhexanoate 4 according to the procedures described for compound 2 in above (See Schemes 1 and 2).

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

Procedure: In a modification of the method described in JCS Perkin Trans. I 1972, 2584, a mixture of 2-hydroxy-hexanoic acid ethyl ester (5 g, 31 mmol), N-bromosuccinimide (12 g, 67 mmol) and catalytic AIBN in anhydrous CCl4 (60 mL) is refluxed. After heating for about 20 minutes, the reaction initiates with evolution of a red-brown gas. After refluxing 4 hours, the resulting mixture is filtered and the filtrate evaporated at reduced pressure to obtain 3-bromo-2-oxo-hexanoic acid ethyl ester as a dark liquid. Step 2. Preparation of 3-(1-propyl)-imidazolo[1,2-a]pyridine-2-carboxylate is refluxed After heating for about 20 minutes After refluxing 4 hours the resulting mixture is filtered the filtrate evaporated at reduced pressure

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

Procedure: In a modification of the method described in JCS Perkin Trans. I 1972, 2584, a mixture of 2-hydroxy-hexanoic acid ethyl ester (5 g, 31 mmol), N-bromosuccinimide (12 g, 67 mmol) and catalytic AIBN in anhydrous CCl4 (60 mL) is refluxed. After heating for about 20 minutes, the reaction initiates with evolution of a red-brown gas. After refluxing 4 hours, the resulting mixture is filtered and the filtrate evaporated at reduced pressure to obtain 3-bromo-2-oxo-hexanoic acid ethyl ester as a dark liquid. Step 2. Preparation of 3-(1-propyl)-imidazolo[1,2-a]pyridine-2-carboxylate is refluxed After heating for about 20 minutes After refluxing 4 hours the resulting mixture is filtered the filtrate evaporated at reduced pressure

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

Procedure: The title compound was prepared from 4′-(2-benzyl-benzofuran-3-yl)-3,5-dibromo-biphenyl-4-ol, and ethyl DL-2-hydroxycaproate, in substantially the same manner, as described in Example 1, steps g-h , and was obtained as a white solid, mp 75-76° C.; MS m/e 645 (M−H)+; was obtained as a white solid, mp 75-76° C.

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

Procedure: The title compound was prepared from 4′-(2-benzyl-benzofuran-3-yl)-3,5-dibromo-biphenyl-4-ol, and ethyl DL-2-hydroxycaproate, in substantially the same manner, as described in Example 1, steps g-h , and was obtained as a white solid, mp 75-76° C.; MS m/e 645 (M−H)+; was obtained as a white solid, mp 75-76° C.

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

Procedure: Imidazole (4.10 g, 60.22 mmol) and TBDMSCl (3.60 g, 23.89 mmol) was added to a stirred solution of 2-hydroxy-hexanoic acid ethyl ester (3.20 g, 19.97 mmol) in DMF (25 mL). The reaction mixture was kept at ambient temperature for 18 hrs. Water and diethyl ether were added and the two phases were separated. The aqueous phase was extracted with diethyl ether. The organic extracts were combined and washed sequentially with 0.5 M HCl and water, dried over MgSO4 and concentrated in vacuo to give the title product (5.30 g), 1H NMR (300 MHz, CDCl3) δ 4.18 (m, 3H), 1.69 (m, 2H), 1.35 (m, 4H), 1.28 (t, 3H), 0.91 (m, 12H), 0.07 (d, 6H). the two phases were separated The aqueous phase was extracted with diethyl ether washed sequentially with 0.5 M HCl and water dried over MgSO4 concentrated in vacuo