1,1-Dichloroethane → HCID 11429521, compound

Participants

Reaction Steps

A mixture of racemic-(trans)-2-(4-aminophenyl)cyclopropanecarboxylic acid (I-1) (0.060 g, 0.339 mmols) and dichloroethane was heated slightly and allowed to cool before addition of 4-[4-(trifluoromethyl)phenyl]-2-furancarbaldehyde (0.075 g, 0.312 mmols). The mixture was stirred for 7 h, followed by addition of sodium triacetoxyborohydride (0.104 g, 0.491 mmols). After 12 h, the mixture was partitioned between water and CH2Cl2 (10 mL each). The aqueous phase was extracted with CH2Cl2 (1×10 mL). The combined organics were dried with MgSO4 and concentrated to give the title compound as a yellow solid (0.139 g, quant). 1H NMR (400 MHz, DMSO-d6): δ 12.01 (s, 1H), 8.23 (s, 1H), 7.75 (d, J=8.24 Hz, 2H), 7.68 (d, J=8.42 Hz, 2H), 6.85 (d, J=8.42 Hz, 2H), 6.81 (s, 1H), 6.56 (d, J=8.61 Hz, 2H), 6.05 (t, J=5.95 Hz, 1H), 4.22 (d, H=5.86 Hz, 2H), 2.18 (m, 1H), 1.58 (m, 1H), 1.27 (m, 1H), 1.16 (m, 1H). APCI m/z 399.93 (MH−).

Provenance & Evidence