反应详情

To 3-methyl-4-(oxetan-3-yl)benzonitrile (500 mg, 2.89 mmol) in ethanol (7.5 mL) was added NaOH (3.0 mL of 5 M, 15 mmol) and the mixture immersed in a 85° C. oil bath. The mixture was heated and stirred for 1 h, concentrated, then diluted with ethyl acetate (20 mL). 6N HCl (˜3 mL) was added to adjust pH to 6. The aqueous layer was extracted with ethyl acetate (2×20 mL), then the combined organics washed with brine (10 mL), dried over MgSO4 and concentrated to give a white solid, which was triturated with ether to give a mixture (2:3 by NMR) of acid 3-methyl-4-(oxetan-3-yl)benzoic acid (500 mg, 14%) and amide. ESI-MS m/z calc. 192.2, found 193.3 (M+1)+; Retention time: 0.87 minutes (3 min run).

1. customimmersed in a 85° C.
2. temperatureThe mixture was heated
3. concentrationconcentrated
4. additiondiluted with ethyl acetate (20 mL)
5. addition6N HCl (˜3 mL) was added
6. extractionThe aqueous layer was extracted with ethyl acetate (2×20 mL)
7. washthe combined organics washed with brine (10 mL)
8. dry with materialdried over MgSO4
9. concentrationconcentrated
10. customto give a white solid, which
11. customwas triturated with ether