反应详情

4-Mercaptobenzoic acid (2.0 g, 13 mmol) was placed in THF (25 ml). DIEA (3.7 g, 28.5 mmol) was added followed by a solution of methyl 10-bromodecanoate (3.44 g, 13 mmol) in THF (10 ml). After 1 h the solvent was removed under vacuum to yield a slurry, which was stored at rt for 3 days. AcOEt (100 ml) and 1 N HCl (50 ml) were added, but the precipitate did not dissolve very well. Sat. NaCl was added and then methanol in order to aid phase separation. The aqueous phase was removed, and DCM was added to the organic phase, but the precipitates still did not dissolve. The organic phase was concentrated under vacuum and dried with toluene by adding and evaporating twice. Drying under vacuum yielded a white solid (4.4 g, quantitative yield).

1. customAfter 1 h the solvent was removed under vacuum
2. customto yield a slurry, which
3. dissolutionthe precipitate did not dissolve very well
4. customphase separation
5. customThe aqueous phase was removed
6. additionDCM was added to the organic phase
7. customthe precipitates still
8. dissolutiondid not dissolve
9. concentrationThe organic phase was concentrated under vacuum
10. dry with materialdried with toluene
11. additionby adding
12. customevaporating twice
13. customDrying under vacuum