In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact.24621-61-2,(S)-Butane-1,3-diol, it is a common compound, a new synthetic route is introduced below.24621-61-2
Example 1 Preparation of (3S)-1-p-Toluenesulfonyloxy-3-triethylsilyloxy-butane (2)To a stirred solution of the (S)-(+)-1,3-butanediol 1 (1 g, 11.1 mmol), DMAP (30 mg, 0.25 mmol) and Et3N (4.6 mL, 3.33 g, 33 mmol) in anhydrous methylene chloride (20 mL) p-toluenesulfonyl chloride (2.54 g, 13.3 mmol) was added at 0 C. The reaction mixture was stirred at 4 C. for 22 h. Methylene chloride was added and the mixture was washed with water, dried (Na2SO4) and concentrated under reduced pressure. A residue was chromatographed on silica gel with hexane/ethyl acetate (8:2, then 1:1) to afford the tosylate (2.31 g, 85% yield) as a colorless oil.To a stirred solution of the tosylate (2.31 g, 9.5 mmol) and 2,6-lutidine (1.2 mL, 1.12 g, 10.5 mmol) in anhydrous methylene chloride (15 mL) triethylsilyl trifluoromethanesulfonate (2.1 mL, 2.51 g, 9.5 mmol) was added at -50 C. The reaction mixture was allowed to warm to room temperature (4 h) and stirring was continued for additional 20 h. Methylene chloride was added and the mixture was washed with water, dried (Na2SO4) and concentrated under reduced pressure. A residue was chromatographed on silica gel with hexane/ethyl acetate (97:3) to afford the product 2 (2.71 g, 80% yield) as a colorless oil:[alpha]D+18.0 (c 2.38, CHCl3); 1H NMR (400 MHz, CDCl3) delta 7.77 (2H, d, J=8.2 Hz, o-HTs), 7.33 (2H, d, J=8.2 Hz, m-HTs), 4.10 (2H, t, J=6.1 Hz, 1-H2), 3.90 (1H, m, 3-H), 2.43 (3H, s, MeTs), 1.72 (2H, m, 2-H2), 1.10 (3H, d, J=6.2 Hz, 4-H3), 0.88 (9H, t, J=8.0 Hz, 3¡ÁSiCH2CH3), 0.50 (6H, q, J=8.0 Hz, 3¡ÁSiCH2CH3); 13C NMR (100 MHz) delta 144.62 (s, p-CTs), 133.03 (s, i-CTs), 129.72 (d, m-CTs), 127.82 (d, o-CTs), 67.78 (t, C-1), 64.46 (d, C-3), 38.47 (t, C-2), 23.82 (q, C-4), 21.52 (q, MeTs), 6.71 (q, SiCH2CH3), 4.77 (t, SiCH2CH3); MS (EI) m/z 359 (5, MH+), 329 (87, M+-C2H5), 259 (100), 233 (54), 197 (50), 179 (74), 163 (40), 149 (48), 135 (38), 115 (53), 91 (71); exact mass calculated for C15H25O4SSi (M+-C2H5) 329.1243, found 329.1239.
In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 24621-61-2, other downstream synthetic routes, hurry up and to see.
Reference£º
Patent; DeLuca, Hector F.; Clagett-Dame, Margaret; Plum, Lori A.; Chiellini, Grazia; Grzywacz, Pawel; US2009/170821; (2009); A1;,
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate