methoxy(methoxymethoxy)methane

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

Procedure: The above-mentioned propanol was then converted into 1-tert-butyl-4-(3-methoxymethoxypropyl)benzene by means of dimethoxymethane, in an analogous manner to that described by J. L. Gras et al. in Synthesis 74, (1985), but using 12 equivalents of dimethoxymethane for 1 equivalent of alcohol. The above-mentioned methoxymethylether was then transformed as described by A. Rieche et al., Chem. Ber. 95, 91 (1962) but using dichloromethane as solvent. The concentration of methoxymethylether in this solvent varied between 0.1 and 0.3 M. The reaction product was purified by chromatography to provide 8-tert-butyl-1,3,4,5-tetrahydro-2-benzoxepine (yield 67%, purety>99%). Gras et al. in Synthesis 74, (1985), The reaction product was purified by chromatography

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

Procedure: The above-mentioned propanol was then converted into 1-tert-butyl-4-(3-methoxymethoxypropyl)benzene by means of dimethoxymethane, in an analogous manner to that described by J. L. Gras et al. in Synthesis 74, (1985), but using 12 equivalents of dimethoxymethane for 1 equivalent of alcohol. The above-mentioned methoxymethylether was then transformed as described by A. Rieche et al., Chem. Ber. 95, 91 (1962) but using dichloromethane as solvent. The concentration of methoxymethylether in this solvent varied between 0.1 and 0.3 M. The reaction product was purified by chromatography to provide 8-tert-butyl-1,3,4,5-tetrahydro-2-benzoxepine (yield 67%, purety>99%). Gras et al. in Synthesis 74, (1985), The reaction product was purified by chromatography

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

Procedure: 5,6-O-Isopropylidene-L-ascorbic acid was protected in the form of methoxymethyl ether according to the procedure of Kulkami et al. (M. G. Kulkami and S. R. Thopate, Tetrahedron, 1996, 52, 1293). A Mitsunobu reaction (C. Cena et al. Bioorg. Med. Chem. 2008, 16, 5199) with 1,1′,2-trisnorsqualenol followed by hydrolysis gives 2-squalenyl ascorbic acid (2-SQ Vit C) at an overall yield of 32%. A Mitsunobu reaction (C. Cena et al. Bioorg. Med. Chem. 2008, 16, 5199) with 1,1′,2-trisnorsqualenol followed by hydrolysis

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

Procedure: 5,6-O-Isopropylidene-L-ascorbic acid was protected in the form of methoxymethyl ether according to the procedure of Kulkami et al. (M. G. Kulkami and S. R. Thopate, Tetrahedron, 1996, 52, 1293). A Mitsunobu reaction (C. Cena et al. Bioorg. Med. Chem. 2008, 16, 5199) with 1,1′,2-trisnorsqualenol followed by hydrolysis gives 2-squalenyl ascorbic acid (2-SQ Vit C) at an overall yield of 32%. A Mitsunobu reaction (C. Cena et al. Bioorg. Med. Chem. 2008, 16, 5199) with 1,1′,2-trisnorsqualenol followed by hydrolysis

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

Procedure: The above-mentioned propanol was then converted into 1-tert-butyl-4-(3-methoxymethoxypropyl)benzene by means of dimethoxymethane, in an analogous manner to that described by J. L. Gras et al. in Synthesis 74, (1985), but using 12 equivalents of dimethoxymethane for 1 equivalent of alcohol. The above-mentioned methoxymethylether was then transformed as described by A. Rieche et al., Chem. Ber. 95, 91 (1962) but using dichloromethane as solvent. The concentration of methoxymethylether in this solvent varied between 0.1 and 0.3 M. The reaction product was purified by chromatography to provide 8-tert-butyl-1,3,4,5-tetrahydro-2-benzoxepine (yield 67%, purety>99%). Gras et al. in Synthesis 74, (1985), The reaction product was purified by chromatography

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

Procedure: The preparation of intermediate 6 is described and illustrated below. The coumarin phenol 7 was converted to the methoxymethyl ether using methoxymethyl chloride and Hunig's base in Dimethylformamide. The free aniline, liberated through hydrogenolysis with 10% Pd/C and hydrogen in tetrahydrofuran from 7, was coupled with acid chloride 9 to give benzamide 10. Subsequent cleavage of the methoxymethyl ether with 4N hydrochloride in dioxane provided phenol 6 in high yield.

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

Procedure: The preparation of intermediate 6 is described and illustrated below. The coumarin phenol 7 was converted to the methoxymethyl ether using methoxymethyl chloride and Hunig's base in Dimethylformamide. The free aniline, liberated through hydrogenolysis with 10% Pd/C and hydrogen in tetrahydrofuran from 7, was coupled with acid chloride 9 to give benzamide 10. Subsequent cleavage of the methoxymethyl ether with 4N hydrochloride in dioxane provided phenol 6 in high yield.

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

Procedure: 5,6-O-Isopropylidene-L-ascorbic acid was protected in the form of methoxymethyl ether according to the procedure of Kulkami et al. (M. G. Kulkami and S. R. Thopate, Tetrahedron, 1996, 52, 1293). A Mitsunobu reaction (C. Cena et al. Bioorg. Med. Chem. 2008, 16, 5199) with 1,1′,2-trisnorsqualenol followed by hydrolysis gives 2-squalenyl ascorbic acid (2-SQ Vit C) at an overall yield of 32%. A Mitsunobu reaction (C. Cena et al. Bioorg. Med. Chem. 2008, 16, 5199) with 1,1′,2-trisnorsqualenol followed by hydrolysis

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

Procedure: The above-mentioned propanol was then converted into 1-tert-butyl-4-(3-methoxymethoxypropyl)benzene by means of dimethoxymethane, in an analogous manner to that described by J. L. Gras et al. in Synthesis 74, (1985), but using 12 equivalents of dimethoxymethane for 1 equivalent of alcohol. The above-mentioned methoxymethylether was then transformed as described by A. Rieche et al., Chem. Ber. 95, 91 (1962) but using dichloromethane as solvent. The concentration of methoxymethylether in this solvent varied between 0.1 and 0.3 M. The reaction product was purified by chromatography to provide 8-tert-butyl-1,3,4,5-tetrahydro-2-benzoxepine (yield 67%, purety>99%). Gras et al. in Synthesis 74, (1985), The reaction product was purified by chromatography