[4-[[tert-butyl(dimethyl)silyl]oxymethyl]phenyl]methanol

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

Procedure: α-[4-(tert-Butyldimethylsilyloxymethyl)-benzyloxy][4-(tert-butyldimethylsilyloxymethyl)styrene] and α-[(tert-Butyldimethylsilyloxymethyl )-benzyloxy][3-(tert-butyldimethylsilyloxymethyl)styrene]. (Formula II, R1 =tert-butyldimethylsilyloxymethylphenyl, R2 =4-tert-butyldimethylsilyloxymethylbenzyl). Methyl 4-(hydroxymethyl)benzoate was treated with tert-butyldimethylsilyl chloride using the general procedure described in Journal of the American Chemical Society, 1972, 94, 6190. The resulting product was reduced with lithium aluminium hydride to afford 4-(tert-butyldimethylsilyloxymethyl)benzyl alcohol. This alcohol was converted into the required compound uising Method C. 1H NMR (CCl4) δ 0.08 (12H, s), 0.91 (18H, s), 4.22 (1H, d, J 2 Hz), 4.68 (5H, br s), 4.90 (2H, s), 7.1-7.6 (8H, m); MS (CH4) 483 (M+ --CH3, 52%), 133 100%).

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

Procedure: α-[4-(tert-Butyldimethylsilyloxymethyl)-benzyloxy][4-(tert-butyldimethylsilyloxymethyl)styrene] and α-[(tert-Butyldimethylsilyloxymethyl )-benzyloxy][3-(tert-butyldimethylsilyloxymethyl)styrene]. (Formula II, R1 =tert-butyldimethylsilyloxymethylphenyl, R2 =4-tert-butyldimethylsilyloxymethylbenzyl). Methyl 4-(hydroxymethyl)benzoate was treated with tert-butyldimethylsilyl chloride using the general procedure described in Journal of the American Chemical Society, 1972, 94, 6190. The resulting product was reduced with lithium aluminium hydride to afford 4-(tert-butyldimethylsilyloxymethyl)benzyl alcohol. This alcohol was converted into the required compound uising Method C. 1H NMR (CCl4) δ 0.08 (12H, s), 0.91 (18H, s), 4.22 (1H, d, J 2 Hz), 4.68 (5H, br s), 4.90 (2H, s), 7.1-7.6 (8H, m); MS (CH4) 483 (M+ --CH3, 52%), 133 100%).

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of oxalyichloride (1.6 ml) in dry dichloromethane (37 ml) was cooled to -70° C. under N2. Dry dimethylsulfoxide (2.5 ml) in dichloromethane (10 ml) and a solution of 4-(tert-butyldimethylsilyloxymethyl)benzylalcohol (24) (3.94 g, 15.6 mmol) in dichloromethane (20 ml) were added carefully. The reaction mixture was stirred at -70° C. for 1 h. trimethylamine (12 ml) was then added. The reaction mixture was allowed to warm up no 0° C. Saturated aqueous sodium bicarbonate (50 ml) was added, the organic layer was separated and the aqueous layer was extracted with dichloromethane (4×50 ml). The combined organic extracts were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography over silica (dichloromethane/hexane; 4:1) to yield 4-butyldimethylsilyloxymethyl)benzaldehyde (25) 3.21 g, 82%); νmax /cm-1 2020s, 2850s, 2730w, 1700s, 1090s; δH (CDCl3) 0.11 (6H, s, SiCH3), 0.94 (9 H, s, tert-butyl), 4.80 (2 H, s, CH2O), 7.47 and 7.84 (4 H, AA'BB', PhH) and 9.98 (1 H, s, CHO); (CDCl3) -5.3, 18.4, 25.9, 64.4, 126.2, 129.8, 135.3, 148.6 and 192.0; m/z 251.1467 M+ +H). was then added the organic layer was separated the aqueous layer was extracted with dichloromethane (4×50 ml) The combined organic extracts were dried over anhydrous sodium sulfate filtered concentrated in vacuo The residue was purified by column chromatography over silica (dichloromethane/hexane; 4:1)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of oxalyichloride (1.6 ml) in dry dichloromethane (37 ml) was cooled to -70° C. under N2. Dry dimethylsulfoxide (2.5 ml) in dichloromethane (10 ml) and a solution of 4-(tert-butyldimethylsilyloxymethyl)benzylalcohol (24) (3.94 g, 15.6 mmol) in dichloromethane (20 ml) were added carefully. The reaction mixture was stirred at -70° C. for 1 h. trimethylamine (12 ml) was then added. The reaction mixture was allowed to warm up no 0° C. Saturated aqueous sodium bicarbonate (50 ml) was added, the organic layer was separated and the aqueous layer was extracted with dichloromethane (4×50 ml). The combined organic extracts were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography over silica (dichloromethane/hexane; 4:1) to yield 4-butyldimethylsilyloxymethyl)benzaldehyde (25) 3.21 g, 82%); νmax /cm-1 2020s, 2850s, 2730w, 1700s, 1090s; δH (CDCl3) 0.11 (6H, s, SiCH3), 0.94 (9 H, s, tert-butyl), 4.80 (2 H, s, CH2O), 7.47 and 7.84 (4 H, AA'BB', PhH) and 9.98 (1 H, s, CHO); (CDCl3) -5.3, 18.4, 25.9, 64.4, 126.2, 129.8, 135.3, 148.6 and 192.0; m/z 251.1467 M+ +H). was then added the organic layer was separated the aqueous layer was extracted with dichloromethane (4×50 ml) The combined organic extracts were dried over anhydrous sodium sulfate filtered concentrated in vacuo The residue was purified by column chromatography over silica (dichloromethane/hexane; 4:1)

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

Procedure: α-[4-(tert-Butyldimethylsilyloxymethyl)-benzyloxy][4-(tert-butyldimethylsilyloxymethyl)styrene] and α-[(tert-Butyldimethylsilyloxymethyl)-benzyloxy][3-(tert-butyldimethylsilyloxymethyl)styrene]. (Formula II, R1 =tert-butyldimethylsilyloxymethylphenyl, R2 =4-tert-butyldimethylsilyloxymethylbenzyl). Methyl 4-(hydroxymethyl)benzoate was treated with tert-butyldimethylsilyl chloride using the general procedure described in Journal of the American Chemical Society, 1972, 94, 6190. The resulting product was reduced with lithium aluminium hydride to afford 4-(tert-butyldimethylsilyloxymethyl)benzyl alcohol. This alcohol was converted into the required compound using Method C. 1H NMR (CCl4) δ 0.08 (12H, s), 0.91 (18H, s), 4.22 (1H, d, J 2 Hz), 4.68 (5H, br s), 4.90 (2H, s), 7.1-7.6 (8H, m); MS (CH4) 483 (M+ -CH3, 52%), 133 100%).

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

Procedure: Methyl 4-(hydroxymethyl)benzoate was treated with tert-butyldimethylsilyl chloride using the general procedure described in Journal of the American Chemical Society, 1972, 94, 6190. The resulting product was reduced with lithium aluminium hydride to afford 4-(tert-butyldimethylsilyloxymethyl)benzyl alcohol. This alcohol was converted into the required compound using Method C. 1H NMR (CCl4) δ0.08 (12H, s), 0.91 (18H, s), 4.22 (1H, d, J 2 Hz), 4.68 (5H, br s), 4.90 (2H, s), 7.1-7.6 (8H, m); MS (CH4) 483 (M+ -CH3, 52%), 133 100% ).

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

Procedure: (Formula II, R1=tert-butyldimethylsilyloxymethylphenyl, R2=4-tert-butyldimethylsilyloxymethylbenzyl). Methyl 4-(hydroxymethyl)benzoate was treated with tert-butyldimethylsilyl chloride using the general procedure described in Journal of the American Chemical Society, 1972, 94, 6190. The resulting product was reduced with lithium aluminium hydride to afford 4-(tert-butyldimethylsilyloxymethyl)benzyl alcohol. This alcohol was converted into the required compound using Method C. 1H NMR (CCl4) δ 0.08 (32H, s), 0391 (18H, s), 4.22 (1H, d, J 2 Hz), 4.68 (5H, br s), 4.90 (2H, a), 7.1-7.6 (8H, m); MS (CH4) 483 (M+−CH3, 52%), 133 100%).

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

Procedure: α-[4-(tert-Butyldimethylsilyloxymethyl)-benzyloxy][4-(tert-butyldimethylsilyloxymethyl)styrene] and α-[(tert-Butyldimethylsilyloxymethyl )-benzyloxy][3-(tert-butyldimethylsilyloxymethyl)styrene]. (Formula II, R1 =tert-butyldimethylsilyloxymethylphenyl, R2 =4-tert-butyldimethylsilyloxymethylbenzyl). Methyl 4-(hydroxymethyl)benzoate was treated with tert-butyldimethylsilyl chloride using the general procedure described in Journal of the American Chemical Society, 1972, 94, 6190. The resulting product was reduced with lithium aluminium hydride to afford 4-(tert-butyldimethylsilyloxymethyl)benzyl alcohol. This alcohol was converted into the required compound uising Method C. 1H NMR (CCl4) δ 0.08 (12H, s), 0.91 (18H, s), 4.22 (1H, d, J 2 Hz), 4.68 (5H, br s), 4.90 (2H, s), 7.1-7.6 (8H, m); MS (CH4) 483 (M+ --CH3, 52%), 133 100%).