反应详情

Using the procedure outlined in Example 33, (R)-2-bromodecanoic acid (0.374 g, 1.49 mmol) was treated with potassium tert-butoxide (0.480 g, 4.28 mmol) in THF (9 mL) at 0° C. Hexanethiol (0.30 mL, 2.02 mmol) was added dropwise and the reaction was stirred for 18 hours. The reaction was poured into 1N HCl (25 mL) and extracted with hexane (2×25 mL). The combined organic layers were washed with NaHCO3 solution (25 mL, 0.5M), followed by HCl (1N, 25 mL) and dried (MgSO4). Following solvent removal, (S)-hexylthiodecanoic acid (0.34 g, 1.18 mmol, 80%) was obtained. This material was judged to be 95% ee.

1. extractionextracted with hexane (2×25 mL)
2. washThe combined organic layers were washed with NaHCO3 solution (25 mL, 0.5M)
3. dry with materialdried (MgSO4)
4. customFollowing solvent removal