Picolyl chloride → trans-6-(2-Pyridyl)methoxy-3-(3-pyridyl)methyl-4-chromanol

HRID 610381Notes

Reaction equation

HRID 610381 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][C@H:8]2[C@H:17]([OH:18])[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([OH:19])[CH:15]=3)[O:10][CH2:9]2)[CH:2]=1.[N:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH2:26]Cl>>[N:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH2:26][O:19][C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[O:10][CH2:9][C@@H:8]([CH2:7][C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)[C@@H:17]2[OH:18]

Participants

3

Reactant 2

HCID 23393Picolyl chlorideHCID 67591831trans-3-(3-Pyridyl)methyl-4,6-chromandiol

Product 1

HCID 67592410trans-6-(2-Pyridyl)methoxy-3-(3-pyridyl)methyl-4-chromanol

Procedure

By the method of Example 5, 500 mg (1.95 mmol) of trans-3-(3-pyridyl methyl)-4,6-chromandiol and 266 mg (2.09 mmol) of 2-picolyl chloride were converted to present title product, purified by flash chromatography on 100 g silica gel using 1:19 CH3OH:ether as eluant to yield 136 mg (20%) of present title compound as an oil.

Sources & evidence

ORD record
ord-2c947df56b1b4069865a692db87bb773
Source dataset
uspto-grants-1999_12
Patent number
US05998451

Reaction notes

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