4-Hydroxymethylpyridine → HCID 18508141, compound

HRID 412101Notes

Reaction equation

HRID 412101 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[N:12]1[CH:17]=[CH:16][C:15]([CH2:18]O)=[CH:14][CH:13]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[N:12]1[CH:17]=[CH:16][C:15]([CH2:18][O:1][C:2]2[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=2)[C:5]([O:7][CH3:8])=[O:6])=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 114724-HydroxymethylpyridineHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 88068Methyl 3-Hydroxybenzoate

Product 1

HCID 18508141HCID 18508141, compoundYield 37.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of methyl 3-hydroxybenzoate (1.0 g, 6.58 mmol), 4-pyridylcarbinol (1.1 g, 9.87 mmol), and triphenylphosphine (2.6 g, 9.87 mmol) in THF (25 mL) at 0° C. was added diisopropyl azodicarboxylate (2.0 g, 9.87 mmol) dropwise. After stirring at room temperature for 16 h, the solution was concentrated and purified by column chromatography (silica gel, ethyl acetate/hexane) to yield the title compound as a white solid (0.599 g, 37%). MS(ESI): 244.1 (M+H)+.

Workup

  1. concentrationthe solution was concentrated
  2. custompurified by column chromatography (silica gel, ethyl acetate/hexane)

Sources & evidence

ORD record
ord-c88210896a9544c1895e74352621cb75
Source dataset
uspto-grants-2003_05
Patent number
US06562842B2

Reaction notes

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