反应详情

A stirred solution of LDA in cyclohexane (1.5 M) was cooled to −20° C., to which a solution of 2-phenoxypropionic acid (10 g, 60.2 mmol) in THF (80.3 mL) was slowly added, keeping the temperature below −10° C. The resulting dianion solution was stirred for 15 min, then a solution of 4-benzyloxy-3-methoxybenzaldehyde (14.58 g, 60.2 mmol) in THF (80.3 mL) was added over 1 h, maintaining temperature below −10° C. Fifteen minutes after completion of aldehyde addition, the reaction mixture was poured onto ice water (200 mL), and extracted using 1:2 Et2O:hexane (500 mL). The aqueous layer was isolated, extracted again with 1:2 Et2O:hexane (240 mL), then acidified with concentrated HCl until pH=3. The product acid was extracted into EtOAc (2×165 mL), which was dried over Na2SO4 and concentrated to an orange paste (16.5 g crude, 67%): MS (EI) 426.2 (M+NH4)+, 407.2 (M−H)−.

1. additionwas slowly added
2. customthe temperature below −10° C
3. temperaturemaintaining temperature below −10° C
4. additionthe reaction mixture was poured onto ice water (200 mL)
5. extractionextracted
6. customThe aqueous layer was isolated
7. extractionextracted again with 1:2 Et2O
8. extractionThe product acid was extracted into EtOAc (2×165 mL), which
9. dry with materialwas dried over Na2SO4
10. concentrationconcentrated to an orange paste (16.5 g crude, 67%)