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Ethyl 2-(4-fluorophenyl)acetimidate hydrochloride

2,4,6-collidine

ethyl chloroformate

→

ethyl N-ethoxycarbonyl-2-(4-fluorophenyl)acetimidate

수율 52.8%

용매

—

hexanes

DCM

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후처리

1. 1
   기타at 0° C
2. 2
   기타The solvent was removed in vacuo
3. 3
   기타sonicated for 10 minutes
4. 4
   기타The solids were removed by filtration through a pad of diatomaceous earth
5. 5
   세척the filter cake was washed with EtOAc (3×10 mL)
6. 6
   농축The combined filtrates were concentrated in vacuo

실험 절차

Ethyl 2-(4-fluorophenyl)acetimidate hydrochloride (1.6 g, 7.4 mmol) was suspended in hexanes (18.5 mL) and DCM (18.5 mL) at 0° C. 2,4,6-collidine (3.9 mL, 29.6 mmol) and ethyl chloroformate (1.6 g, 14.8 mmol) were added sequentially and the reaction mixture was allowed to warm to RT and stirred for 12 h. The solvent was removed in vacuo and the residue was suspended in EtOAc (100 mL) and sonicated for 10 minutes. The solids were removed by filtration through a pad of diatomaceous earth and the filter cake was washed with EtOAc (3×10 mL). The combined filtrates were concentrated in vacuo to afford ethyl N-ethoxycarbonyl-2-(4-fluorophenyl)acetimidate (0.99 g, 52.7%) as an amorphous yellow solid. 1H NMR (400 MHz, DMSO-d6): δ 7.25 (dd, J=8.5, 5.6 Hz, 2H), 7.13 (t, J=8.8 Hz, 2H), 4.06 (q, J=7.1 Hz, 2H), 4.04 (q, J=7.1 Hz, 2H), 3.66 (s, 2H), 1.15 (t, J=7.1 Hz, 3H), 1.14 (t, J=7.1 Hz, 3H).

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