1,4,7,10,13,16-hexaoxacyclooctadec-2-ylmethanol

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

Procedure: Compound 29 was prepared by a method similar to that described by Montanari and Tundo20 for the synthesis of 2-(hydroxy methyl)-1,4,7,10,13,16-hexaoxacyclooctadecane. KBF4 complex, (2-(hydroxy methyl)-18-crown-6). To a solution of compound 23 (10.0 g, 0.038 mol.) in dichloromethane (100 ml) was added tetrafluoroboric acid-diethyl ether complex (54% in diethyl ether), (13.7 ml). The mixture was left stirring at room temperature for 20 minutes. The acid was neutralized with solid potassium carbonate, inorganic salts were filtered, the solvent was removed by rotary evaporation to give a pale yellow oil. The crude product was distilled under vacuum (bpt. 94°-95° C., 0.02 torr) to give a colorless liquid (18.75 g, 78%): 1H-NMR (CDCl3), d (ppm) 3.5-3.9 (m, 13H), 3.35-3.4 (s, 6H), 2.75-2.8 (s, 1H); 13C-NMR (CDCl3), d (ppm) 79.56, 72.07, 71.73, 71.16, 70.59, 69.35, 62.40, 58.83, 58.75. The mixture was left were filtered the solvent was removed by rotary evaporation to give a pale yellow oil The crude product was distilled under vacuum (bpt. 94°-95° C., 0.02 torr)

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

Procedure: Compound 29 was prepared by a method similar to that described by Montanari and Tundo20 for the synthesis of 2-(hydroxy methyl)-1,4,7,10,13,16-hexaoxacyclooctadecane. KBF4 complex, (2-(hydroxy methyl)-18-crown-6). To a solution of compound 23 (10.0 g, 0.038 mol.) in dichloromethane (100 ml) was added tetrafluoroboric acid-diethyl ether complex (54% in diethyl ether), (13.7 ml). The mixture was left stirring at room temperature for 20 minutes. The acid was neutralized with solid potassium carbonate, inorganic salts were filtered, the solvent was removed by rotary evaporation to give a pale yellow oil. The crude product was distilled under vacuum (bpt. 94°-95° C., 0.02 torr) to give a colorless liquid (18.75 g, 78%): 1H-NMR (CDCl3), d (ppm) 3.5-3.9 (m, 13H), 3.35-3.4 (s, 6H), 2.75-2.8 (s, 1H); 13C-NMR (CDCl3), d (ppm) 79.56, 72.07, 71.73, 71.16, 70.59, 69.35, 62.40, 58.83, 58.75. The mixture was left were filtered the solvent was removed by rotary evaporation to give a pale yellow oil The crude product was distilled under vacuum (bpt. 94°-95° C., 0.02 torr)

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

Procedure: Compound 29 was prepared by a method similar to that described by Montanari and Tundo20 for the synthesis of 2-(hydroxy methyl)-1,4,7,10,13,16-hexaoxacyclooctadecane. KBF4 complex, (2-(hydroxy methyl)-18-crown-6). To a solution of compound 23 (10.0 g, 0.038 mol.) in dichloromethane (100 ml) was added tetrafluoroboric acid-diethyl ether complex (54% in diethyl ether), (13.7 ml). The mixture was left stirring at room temperature for 20 minutes. The acid was neutralized with solid potassium carbonate, inorganic salts were filtered, the solvent was removed by rotary evaporation to give a pale yellow oil. The crude product was distilled under vacuum (bpt. 94°-95° C., 0.02 torr) to give a colorless liquid (18.75 g, 78%): 1H-NMR (CDCl3), d (ppm) 3.5-3.9 (m, 13H), 3.35-3.4 (s, 6H), 2.75-2.8 (s, 1H); 13C-NMR (CDCl3), d (ppm) 79.56, 72.07, 71.73, 71.16, 70.59, 69.35, 62.40, 58.83, 58.75. The mixture was left were filtered the solvent was removed by rotary evaporation to give a pale yellow oil The crude product was distilled under vacuum (bpt. 94°-95° C., 0.02 torr)