3-Pyridinemethanol → Methyl 4-[3-(2-(3-pyridylmethyloxy)phenyl)propyl]benzoate

HRID 2395057Notes

Reaction equation

HRID 2395057 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][CH2:10][C:11]1[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=1.O[CH2:22][C:23]1[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[N:25]1[CH:26]=[CH:27][CH:28]=[C:23]([CH2:22][O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[CH2:8][CH2:9][CH2:10][C:11]2[CH:12]=[CH:13][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:19][CH:20]=2)[CH:24]=1

Participants

6

Reactant 4

HCID 75103-PyridinemethanolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 18973735Methyl 4-(3-(2-hydroxyphenyl)propyl]benzoate

Product 1

HCID 18973886Methyl 4-[3-(2-(3-pyridylmethyloxy)phenyl)propyl]benzoateYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 4-[3-(2-hydroxyphenyl)propyl]benzoate (1.35 g, 5 mmol) was dissolved in 0.2 ml of THF. The solution was treated with 3-hydroxymethylpyridine (0.6 g, 5.5 mmol) and triphenylphosphine (1.44 g, 5.5 mmol). To this mixture was added slowly diethylazodicarboxylate (0.96 g, 5.5 mmol). The reaction mixture was stired for 72 hours and the solvent was evaporated. The amide residue was purified by chromatography (methanol, dichloromethane) to give methyl 4-[3-(2-(3-pyridylmethyloxy)phenyl)propyl]benzoate as a pink oil (1.03 g, 57%) MS (CI+):362 [M+H]+.

Workup

  1. customthe solvent was evaporated
  2. customThe amide residue was purified by chromatography (methanol, dichloromethane)

Sources & evidence

ORD record
ord-e4a55f478bf24d24af2bb065a163ef65
Source dataset
uspto-grants-1998_09
Patent number
US05811459

Reaction notes

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