Table 1.
| |||||
---|---|---|---|---|---|
entry | acylating reagent | product | R | yield | |
1 | (CH3CO)2O | 3a | 2a | Me | 78 |
2 | (CH3CH2CO)2O | 3b | 2b | Et | 78 |
3 | (CH3CH2CH2CO)2O | 3c | 2c | Pr | 73 |
4 | [(CH3)2CHCO]2O | 3d | 2d | iPr | 78 |
5 | TBSO(CH2)4COOSu | 3e | 2e | TBSO(CH2)4 | 68 |
6 | 3f | 2f | 91 |
Compound 1 was treated with NaH (1.1 equiv) in DMF for 1 h, then an acylating reagent (1.1 equiv) was added. The yields refer to isolated yields.