Methyl iodide → HCID 15135018, compound

To methyl 3-hydroxy-2-prop-2-en-1-ylbenzoate (10.3 g, 53.6 mmol, M. A. Eissenstat et al., J. Med. Chem. 1995, 38, 3094-3105) and cesium carbonate (26.2 g, 80.4 mmol) in DMF (100 ml) was added methyl iodide (15.2 g, 102.2 mmol). The reaction mixture was stirred at room temperature for 18 h, then filtered and concentrated. The residue was partitioned between ethyl acetate (250 mL) and water (100 mL). The layers were separated, the organic layer was washed with 5% lithium chloride (2×100 mL) and brine (100 mL), dried over sodium sulfate, and concentrated to provide methyl 3-(methyloxy)-2-prop-2-en-1-ylbenzoate (10.3 g, 93% yield) as a pale yellow oil. 1H NMR (400 MHz, CDCl3): δ 7.41 (m, 1H), 7.24 (m, 1H), 7.02 (m, 1H), 6.97 (m, 1H), 4.97 (m, 2H), 3.88 (s, 3H), 3.85 (s, 3H), 3.73 (m, 2H).

1. filtrationfiltered
2. concentrationconcentrated
3. customThe residue was partitioned between ethyl acetate (250 mL) and water (100 mL)
4. customThe layers were separated
5. washthe organic layer was washed with 5% lithium chloride (2×100 mL) and brine (100 mL)
6. dry with materialdried over sodium sulfate
7. concentrationconcentrated

ORD record

ord-0907691a163241fbb6ea880329c83036

Source dataset

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08012956B2