2-(Bromomethyl)-6-chloro-pyridine → trans-3-Benzyl-6-(6-chloro-2-pyridyl)methoxy-4-chromanol

HRID 610377Notes

Reaction equation

HRID 610377 reaction equation
[CH2:1]([C@H:8]1[C@H:17]([OH:18])[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([OH:19])[CH:15]=2)[O:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([CH2:27]Br)[N:22]=1>>[CH2:1]([C@H:8]1[C@H:17]([OH:18])[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:19][CH2:27][C:23]3[CH:24]=[CH:25][CH:26]=[C:21]([Cl:20])[N:22]=3)[CH:15]=2)[O:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 220327372-(Bromomethyl)-6-chloro-pyridineHCID 67592272trans-3-Benzyl-4,6-chromandiol

Product 1

HCID 86745188trans-3-Benzyl-6-(6-chloro-2-pyridyl)methoxy-4-chromanol

Procedure

By the method of Example 5, 0.50 g (1.96 mmol) of trans-3-benzyl-4,6-chromandiol and 445 mg (2.16 mmol) of 2-chloro-6-(bromomethyl)pyridine were converted to present title product purified by recrystallization from CH2Cl2 /hexane, to yield 0.50 g (67%) of present title compound, m.p. 117-119° C.

Sources & evidence

ORD record
ord-ff626d1f06414309a4b61abacb382c82
Source dataset
uspto-grants-1999_12
Patent number
US05998451

Reaction notes

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