2,6-Diisopropyl-3hydroxymethyl-4-(4-fluorophenyl)-5-[2(E)-phenyl-ethenyl]pyridine → 2,6-Diisopropyl-3-hydroxymethyl-4-(4-fluorophenyl)-5-(2-phenylethyl)pyridine

HRID 324812Notes

Reaction equation

HRID 324812 reaction equation
[CH:1]([C:4]1[C:9]([CH2:10][OH:11])=[C:8]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[C:7](/[CH:19]=[CH:20]/[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:6]([CH:27]([CH3:29])[CH3:28])[N:5]=1)([CH3:3])[CH3:2]>C(OCC)(=O)C.CCCCCC>[CH:1]([C:4]1[C:9]([CH2:10][OH:11])=[C:8]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[C:7]([CH2:19][CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[C:6]([CH:27]([CH3:29])[CH3:28])[N:5]=1)([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 220049932,6-Diisopropyl-3hydroxymethyl-4-(4-fluorophenyl)-5-[2(E)-phenyl-ethenyl]pyridine

Product 1

HCID 220049912,6-Diisopropyl-3-hydroxymethyl-4-(4-fluorophenyl)-5-(2-phenylethyl)pyridine

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

The title compound was prepared from 2,6-diisopropyl-3-hydroxymethyl-4-(4-fluorophenyl)-[2(E)-phenylethenyl]pyridine (Example 34) according to the procedure described in Example 1, Step H. 1H NMR (300 MHz, CDCl3): δ7.19 (m, 7 H), 6.86 (m, 2 H), 4.36 (d, J=5.5 Hz, 2 H), 3.44 (sept, J=6.6 Hz, 1 H), 3.35 (sept, J=6.6 Hz, 1 H), 2.58 (m, 4 H), 1.35 (d, J=6.6 Hz, 6 H), 1.34 (d, J=6.6 Hz, 6 H), 1.19 (t, J =5.5 Hz, 1 H). FAB-MS: calculated for (C26H30FNO) 391, found 392 (M+H). Anal. Calcd for C26H30FNO: C, 79.76; H, 7.72; N, 3.58. Found: C, 79.57; H, 7.61; N, 3.44. mp 158-159° C. Rf=0.3 (20% ethyl acetate/hexane).

Sources & evidence

ORD record
ord-61ab6d126e7548c2b489110941698c41
Source dataset
uspto-grants-2001_04
Patent number
US06218431B1

Reaction notes

Loading…