5-(Oct-1-ynyl)-2-tritylisoindoline → 2,2,2-Trifluoro-1-(6-octyl-3,4-dihydroisoquinolin-2(1H)-yl)ethanone
Reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]([N:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:15]#[C:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH:11]=2)[CH2:6]1)=[O:4].C(C1C=C2C(=CC=1)CN(C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C2)#CCCCCCC>>[F:24][C:2]([F:1])([F:23])[C:3]([N:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH:11]=2)[CH2:6]1)=[O:4]Participants
3
Procedure
When the product of Step C is substituted for 5-(oct-1-ynyl)-2-tritylisoindoline in Example 2, Step E, the identical process afforded the title compound in 75% yield after purification of the crude product by FCC (SiO2; EtOAc/hexane, 3:7)., as a colourless foam. 1H-NMR (CDCl3) 0.86 (tr, 3H, J=6.9 Hz); 1.28 (m, 10H); 1.56 (m, 2H); 2.55 (tr, 2H, J=6.9 Hz); 2.87-2.93 (m, 2H); 3.79-3.88 (m, 2H); 4.6-4.8 (m, 2H); 6.8-7.16 (m, 3H).