Ammonia → trans-[2-(4-Bromophenyl)cyclopropyl]methanol

반응식

[Br:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[CH2:10][OH:11])=[CH:4][CH:3]=1.[C:12]1(C=CCO)C=CC=CC=1.N>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]2[CH2:12][C@H:9]2[CH2:10][OH:11])=[CH:6][CH:7]=1

참가 물질

반응물 3

HCID 222Ammonia

HCID 3083-Phenylprop-2-En-1-Ol

HCID 11183465(2E)-3-(4-bromophenyl)prop-2-en-1-ol

생성물 1

HCID 18651197trans-[2-(4-Bromophenyl)cyclopropyl]methanol

실험 절차

The title compound was prepared by the method of A. B. Charette and H. Lebel (Organic Synthesis, 1998, 76, 86-96) substituting trans-3-(4-Bromophenyl) prop-2-en-1-ol (the product from Example 1A) for 3-Phenyl-prop-2-en-1-ol. 1H NMR (300 MHz, CDCl3): δ 0.92-1.0 (m, 2H), 1.45-1.48 (m, 2H), 1.76-1.85 (m, 1H), 3.61 (d, J=7.5 Hz, 2H), 6.95 (d, J=9 Hz, 2H), 7.37 (d, J=9 Hz, 2H). MS (DCl—NH3) m/z 228 (M+H)+.