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温度

0 °C

A mixture of 5-methyl-2,3-dihydrobenzofuran (1b) (2.7 g, 20 mmol) in TFA (50 mL) was cooled to 0° C., NaNO2 (2.5 g, 36 mmol) was added thereto. Then it was warmed up to ambient temperature and stirred for 12 h. The mixture was concentrated, poured into water (50 mL), extracted with EtOAc (150 mL), washed with brine, dried and concentrated. The residue was purified by column chromatography on silica gel eluting with hexanes/EtOAc (10:1) to give the title compound (1c).

1. temperatureThen it was warmed up to ambient temperature
2. concentrationThe mixture was concentrated
3. additionpoured into water (50 mL)
4. extractionextracted with EtOAc (150 mL)
5. washwashed with brine
6. customdried
7. concentrationconcentrated
8. customThe residue was purified by column chromatography on silica gel eluting with hexanes/EtOAc (10:1)