4-Bromobenzyl alcohol → HCID 69300322, compound

HRID 2218124Notes

Reaction equation

Br[C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1.[C:10]([O:15][CH3:16])(=[O:14])/[CH:11]=[CH:12]/[CH3:13]>>[CH3:16][O:15][C:10](=[O:14])/[CH:11]=[C:12](/[C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1)\[CH3:13]

Participants

Reactant 2

HCID 701194-Bromobenzyl alcohol

HCID 638132Methyl Crotonate

Product 1

HCID 69300322HCID 69300322, compound

Procedure

For the above synthesis, (E)-3-{4-[3-(4-nitrophenyl)-2H-oxo-2-pyridin-1-yl]phenyl}but-2-enoic acid methyl ester was prepared from P3 and (E)-3-(4-methanesulfonyloxymethylphenyl)but-2-enoic acid methyl ester by the method of Preparation 7, and (E)-3-(4-methanesulfonyloxymethylphenyl)but-2-enoic acid methyl ester was prepared from (E)-3-(4-hydroxymethylphenyl)but-2-enoic acid methyl ester and methanesulfonyl chloride analogously to the method of Preparation 6 (in this case mostly the mesylate was isolated rather than the chloride). (E)-3-(4-hydroxymethylphenyl)but-2-enoic acid methyl ester was prepared analogously to the method of Preparation 4 from 4-bromobenzyl alcohol and methyl crotonate.

Sources & evidence

ORD record: ord-243b60c5bb894e3dbca8ce039d36d106
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07410984B2

Reaction notes

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