4-Chloropyridine → HCID 57081329, compound

HRID 342492Notes

Reaction equation

HRID 342492 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[Li+].CC([N-]C(C)C)C.[CH3:16][O:17][C:18]1[CH:25]=[CH:24][C:21]([CH:22]=O)=[CH:20][CH:19]=1>CO>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[CH2:22][C:21]1[CH:24]=[CH:25][C:18]([O:17][CH3:16])=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 122884-ChloropyridineHCID 312444-MethoxybenzaldehydeHCID 2724682Lithium diisopropylamide

Product 1

HCID 57081329HCID 57081329, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Chloropyridine is treated sequentially with LDA (1.1 molar equivalents) and 4-methoxybenzaldehyde (1 molar equivalent). The resulting carbinol is isolated and deoxygenated with triethylsilane (10 molar equivalents) and 50% trifluoroacetic acid in methylene chloride to provide the title compound.

Workup

  1. customdeoxygenated with triethylsilane (10 molar equivalents) and 50% trifluoroacetic acid in methylene chloride

Sources & evidence

ORD record
ord-80b359fd0b3e46439649448628deaec6
Source dataset
uspto-grants-1999_01
Patent number
US05859015

Reaction notes

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