4-Penten-1-OL → 5-Trimethylsilyloxy-2-(4-[5-hydroxy-1-pentenyl]phenyl)pyridine

HRID 1728273Notes

Reaction equation

HRID 1728273 reaction equation
[CH3:1][Si:2]([CH3:18])([CH3:17])[O:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:15]=[CH:14][C:13](Br)=[CH:12][CH:11]=2)=[N:8][CH:9]=1.[CH2:19]([OH:24])[CH2:20][CH2:21][CH:22]=[CH2:23].C(=O)(O)[O-].[Na+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CN1CCCC1=O>[CH3:1][Si:2]([CH3:18])([CH3:17])[O:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:15]=[CH:14][C:13]([CH:23]=[CH:22][CH2:21][CH2:20][CH2:19][OH:24])=[CH:12][CH:11]=2)=[N:8][CH:9]=1

Participants

7

Reactant 3

HCID 131814-Penten-1-OLHCID 516892Sodium BicarbonateHCID 190171025-Trimethylsilyloxy-2-(4-bromophenyl)pyridine

Product 1

HCID 543181965-Trimethylsilyloxy-2-(4-[5-hydroxy-1-pentenyl]phenyl)pyridineYield 88.6%

Reagents, catalysts & solvents 3

HCID 11776TriphenylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

6.0 g of 5-trimethylsilyloxy-2-(4-bromophenyl)pyridine, 2.5 g of 4-penten-1-ol, 4 g of sodium bicarbonate solution, 20 ml of N-methylpyrrolidone, 0.03 g of palladium(II) acetate and 0.11 g of triphenylphosphine were reacted in an analogous manner to Example 1(b) to give 5.4 g of 5-trimethylsilyloxy-2-(4-[5-hydroxy-1-pentenyl]phenyl)pyridine.

Sources & evidence

ORD record
ord-3a00e3a2732e434ea8cf206169ca0e65
Source dataset
uspto-grants-1994_07
Patent number
US05326497

Reaction notes

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