Methyl phenylacetate → HCID 68870927, compound

Temperature

0 °C

To a stirring solution of freshly prepared lithium diisopropylamine (76.5 mmol) in 500 mL of tetrahydrofuran at 0° C. was added methyl phenylacetate (10.44 g, 69.50 mmol) in 125 mL tetrahydrofuran dropwise over 30 minutes. After stirring at 0° C. for 1 hour the reaction mixture was cooled to −78° C. and treated with 50 mL of hexamethylphosphoric triamide followed by the dropwise addition of bromomethyl cyclobutane (9.37 mL, 83.4 mmol) and LiI (200 mg). The reaction mixture was stirred for 18 hours warming to 25° C. The reaction was quenched over 1 L of water containing 250 mL of sat. NH4Cl and extracted 3× with ethyl acetate. The combined organic layers were washed sequentially with saturated sodium bicarbonate, brine, and dried over MgSO4 yielding the crude product as an oil that was used without further purification. 1H NMR (300 MHz, CDCl3): δ ppm 1.59 m, 2 H) 1.89 m, 5 H) 2.17 m, 2 H) 3.47 (t, J=7.54 Hz, 1 H) 3.64 (s, 3 H) 7.31 (m, 5 H). MS (ESI+) m/z=236 (M+NH4)+.

1. temperaturewas cooled to −78° C.
2. stirringThe reaction mixture was stirred for 18 hours
3. temperaturewarming to 25° C
4. customThe reaction was quenched over 1 L of water containing 250 mL of sat. NH4Cl
5. extractionextracted 3× with ethyl acetate
6. washThe combined organic layers were washed sequentially with saturated sodium bicarbonate, brine
7. dry with materialdried over MgSO4 yielding the crude product as an oil that
8. customwas used without further purification

ORD record

ord-ea5c2f19af4c46b184c6068821e1c4c2

Source dataset

uspto-grants-2008_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07378414B2