2,6-Diethyl-3-hydroxymethyl4-phenyl-5-(1-ethenyl)pyridine → 2,5,6-Triethyl-3-hydroxymethyl-4-phenylpyridine

HRID 324800Notes

Reaction equation

HRID 324800 reaction equation
[CH2:1]([C:3]1[C:8]([CH2:9][OH:10])=[C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:6]([CH:17]=[CH2:18])=[C:5]([CH2:19][CH3:20])[N:4]=1)[CH3:2]>C(OCC)(=O)C.CCCCCC>[CH2:1]([C:3]1[C:8]([CH2:9][OH:10])=[C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:6]([CH2:17][CH3:18])=[C:5]([CH2:19][CH3:20])[N:4]=1)[CH3:2]

Participants

3

Reactant 1

HCID 220049462,6-Diethyl-3-hydroxymethyl4-phenyl-5-(1-ethenyl)pyridine

Product 1

HCID 220051082,5,6-Triethyl-3-hydroxymethyl-4-phenylpyridine

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

The title compound was prepared from 2,6-diethyl-3-hydroxymethyl-4-phenyl-5-(1-ethenyl)pyridine (Example 8) according to the procedure described in Example 1, Step H. 1H NMR (300 MHz, CDCl3): δ7.44 (m, 3 H), 7.18 (m, 2 H), 4.33 (d, J=6 Hz, 2 H), 2.97 (q, J=8 Hz, 2 H), 2.86 (q, J=8 Hz, 2 H), 2.36 (q, J=328 Hz, 2 H), 1.34 (m, 7 H), 0.93 (t, J=8 Hz, 3 H). FAB-MS: calculated for (C18H23NO) 269, found 270 (M+H). Anal. Calcd for C18H23NO: C, 80.26; H, 8.61; N, 5.20. Found: C, 79.70; H, 8.54; N, 5.08. mp 100° C. Rf=0.4 (50% ethyl acetate/hexane).

Sources & evidence

ORD record
ord-a7f5b6ba685d4c40afb013f7e62e62e5
Source dataset
uspto-grants-2001_04
Patent number
US06218431B1

Reaction notes

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