Study of the synthesis of 2-alkoxy-3-enamine derivatives of long chain, unsaturated alcohols in DCM (20 mL) using 6-chloro-3-formylchromone (1) and 2-amino-6-methoxybenzothiazole (2) as substrates.
| Entry | Alcohol (eq.) | Time | Product | Yield (%) |
|---|---|---|---|---|
| 1 | 1-Octanol (1) | 10 h | 3bi | 11 |
| 2 | 1-Octanol (5) | 10 h | 3bi | 12 |
| 3 | 1-Octanol (10) | 10 h | 3bi | 12 |
| 4 | Benzyl alcohol (1) | 7 h | —a | — |
| 5 | 4-ChloroPhenol (1) | 10 h | —a | — |
| 6 | Geraniol (1) | 10 h | 3bjb,c | 7 |
| 7 | 5-Hexyne-1-ol (1) | 10 h | 3bkb,c,d | 6 |
a
Difficult to purify.
b
2-Amino-4-chlorobenzothiazole.
c
Purified by column chromatography.
d
3-Formylchromone.