Aluminium lithium hydride → 1-(Trifluoromethyl)cyclopropanecarboxaldehyde

Temperature

0 °C

To a solution of N-methoxy-N-methyl-1-(trifluoromethyl)cyclopropanecarboxamide (0.23 g, 1.162 mmol) in diethyl ether (3 mL, aldrich) at 0° C. under Ar(g) was added lithium aluminium hydride (1.0 M solution in THF; 1.39 mL, 1.39 mmol, aldrich) dropwise. After completed addition the reaction was then stirred at 0° C. for 45 min. The reaction was quenched with a solution of KHSO4 (1M) at −78° C. and gradually warmed to RT and stirred for 30 min. The reaction was extracted with diethyl ether (2×10 mL). The combined organic extracts were dried over MgSO4, concentrated, and dried in vacuo to afford 62 mg of the title compound as a light yellow liquid, which was used in the next step without further purification. 1H NMR (CHLOROFORM-d) δ: 9.69 (s, 1H), 1.43 (m, 2H), 1.21 (t, J=7.0 Hz, 2H)

1. additionaddition the reaction
2. customThe reaction was quenched with a solution of KHSO4 (1M) at −78° C.
3. temperaturegradually warmed to RT
4. stirringstirred for 30 min
5. extractionThe reaction was extracted with diethyl ether (2×10 mL)
6. dry with materialThe combined organic extracts were dried over MgSO4
7. concentrationconcentrated
8. customdried in vacuo

ORD record

ord-9d04e021b71f42f99ee0047ba1ecc4fb

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09085576B2