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C4–OH protection as benzoate.
 | |||
| entry | reagents and conditions | product | yield |
| 1 | benzoyl chloride (1.5 equiv), pyridine (0.4 M), 65 °C, 12 h | 10 | 47% |
| 2a | benzoyl chloride (2.6 equiv), NEt(iPr)2 (3.0 equiv), CH2Cl2, 40 °C, 12 h | 9 | <20% |
| 3 | benzoic acid (1.8 equiv), DCC (1.8 equiv), DMAP (0.1 equiv), CH2Cl2, 20 °C, 12 h |
9 | 82% |
aStarting material 8 was recovered in ca. 80% yield.
