1-(Trifluoromethyl)cyclopropane-1-carboxylic acid → 1-(Trifluoromethyl)cyclopropanemethanol

Temperature

40 °C

A solution of 1-(trifluoromethyl)cyclopropane-1-carboxylic acid (3 g, 19.47 mmol) in THF (32.4 mL) was treated with borane-THF complex (1.0 M, 31.2 mL, 31.2 mmol) and heated at 40° C. overnight. The mixture was cooled in an ice bath, carefully quenched with satd. NH4Cl, filtered through diatomaceous earth and rinsed well with EtOAc. The filtrate was extracted with EtOAc (2×) and the combined organics were washed with satd. NaHCO3, then brine, dried over Na2SO4 and concentrated to afford (1-(trifluoromethyl)cyclopropyl)methanol (2.46 g, 90%). 1H NMR (400 MHz, DMSO-d6): δ 4.93 (t, J=6.0 Hz, 1H), 3.52 (d, J=6.0 Hz, 2H), 0.86-0.75 (m, 4H).

1. temperatureThe mixture was cooled in an ice bath
2. customcarefully quenched with satd
3. filtrationNH4Cl, filtered through diatomaceous earth
4. washrinsed well with EtOAc
5. extractionThe filtrate was extracted with EtOAc (2×)
6. washthe combined organics were washed with satd
7. dry with materialNaHCO3, then brine, dried over Na2SO4
8. concentrationconcentrated

ORD record

ord-93ad7bf4a0384cd4b0c69457e97f6e62

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09382228B2