4-Hydroxymethylpyridine → HCID 22054344, compound
Reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][OH:8])=[CH:3][CH:2]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.[CH3:40][O:41][C:42]1[C:43]([CH3:70])=[C:44]([C:61]([O:68][CH3:69])=[C:62]([O:66][CH3:67])[C:63]=1[O:64][CH3:65])[CH2:45][C:46]1[CH:47]=[CH:48][C:49](O)=[C:50]([CH:59]=1)[C:51]([N:53]1[CH2:58][CH2:57][CH2:56][CH2:55][CH2:54]1)=[O:52].[OH-].[Na+]>C1C=CC=CC=1>[CH3:40][O:41][C:42]1[C:43]([CH3:70])=[C:44]([C:61]([O:68][CH3:69])=[C:62]([O:66][CH3:67])[C:63]=1[O:64][CH3:65])[CH2:45][C:46]1[CH:47]=[CH:48][C:49]([O:8][CH2:7][C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)=[C:50]([CH:59]=1)[C:51]([N:53]1[CH2:58][CH2:57][CH2:56][CH2:55][CH2:54]1)=[O:52]Participants
7
Procedure
4-Pyridinemethanol (0.254 g, 2.33 mmol), triphenylphosphine (0.611 g, 2.33 mmol) and diethylazodicarboxylate (0.406 g, 2.33 mmol) were added to a benzene solution (30 ml) of N-[5-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-hydroxybenzoyl]piperidine (0.500 g, 1.17 mmol) and the resulting solution was stirred at room temperature for 12 hours. The reaction solution was poured into an aqueous 2N sodium hydroxide solution (15 ml) and then extracted with methylene chloride. The extract was washed with water and then dried, and the solvent was removed by distillation. The obtained residue was purified by silica gel column chromatography (hexand:ethyl acetate=1:5) to obtain the titled compound (0.375 g, 0.721 mmol, 62%).
Workup
- extractionextracted with methylene chloride
- washThe extract was washed with water
- customdried
- customthe solvent was removed by distillation
- customThe obtained residue was purified by silica gel column chromatography (hexand:ethyl acetate=1:5)
Sources & evidence
- ORD record
- ord-1439ede3cdf14fd5ba63d6ce4e697944
- Source dataset
- uspto-grants-2006_06
- Patent number
- US07064124B2
Reaction notes
Loading…