反应详情

温度

55 °C

To a 12 L flask equipped with a condenser and overhead stirrer was added (S)-methyl-2-hexylthiodecanoate (302.5 g, 1.00 mol), and 3 L of dry acetonitrile. To this solution was added sodium iodide (600 g, 4.00 mol) and iodine (25.4 g, 0.10 mol) followed by chlorotrimethylsilane (543 g, 635 ml, 5.00 mol). The reaction was heated to an internal temperature of 55° C. After 12 hours, an additional portion of chlorotrimethylsilane (130 g, 152 mL, 1.20 mol) was added and heating continued for 8 hours. The reaction was cooled to 0° C., 6 L of hexane was added followed by 1 L of ice water, and the layers were allowed to separate. The top hexane layer was separated and set aside. The combined CH3CN/water layers were extracted with hexane (2×6 L). The combined hexane layers were washed with 1 L of water, 0.1M Na2S2O3 (2×3 L) and once with 3 L of 1:1 brine/water. The combined hexane extracts were dried with MgSO4, filtered and concentrated to give (S)-2-hexylthiodecanoic acid (260 g, 0.90 mol, 90%) a colorless oil: [α]D =-59.40° (C=1, MeOH); 1H NMR δ3.19 (m, 1H), 2.63 (m, 2H), 1.95-1.18 (m, 22H), 0.95 (m, 6H).

1. customTo a 12 L flask equipped with a condenser and overhead stirrer
2. temperatureheating
3. waitcontinued for 8 hours
4. temperatureThe reaction was cooled to 0° C.
5. customto separate
6. customThe top hexane layer was separated
7. extractionThe combined CH3CN/water layers were extracted with hexane (2×6 L)
8. washThe combined hexane layers were washed with 1 L of water, 0.1M Na2S2O3 (2×3 L) and once with 3 L of 1:1 brine/water
9. dry with materialThe combined hexane extracts were dried with MgSO4
10. filtrationfiltered
11. concentrationconcentrated