Dimethylformamide → 2-(7-(2-Propenyloxy)naphthyloxymethyl)-3-pyridinepropanol

HRID 1600899Notes

Reaction equation

HRID 1600899 reaction equation
[CH2:1]([O:4][C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][C:9](O)=[CH:10][CH:11]=2)[CH:6]=1)[CH:2]=[CH2:3].[H-].[Na+].[O:18]1C[CH:19]1[CH2:21][CH2:22][C:23]1[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=1.CN(C)[CH:31]=[O:32]>>[CH2:1]([O:4][C:5]1[CH:6]=[C:7]2[C:12]([CH:11]=[CH:10][CH:9]=[C:8]2[O:32][CH2:31][C:24]2[C:23]([CH2:22][CH2:21][CH2:19][OH:18])=[CH:28][CH:27]=[CH:26][N:25]=2)=[CH:13][CH:14]=1)[CH:2]=[CH2:3]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 10877288HCID 10877288, compoundHCID 111716387-(2-Propenyloxy)-2-naphthalenol

Product 1

HCID 867547402-(7-(2-Propenyloxy)naphthyloxymethyl)-3-pyridinepropanol

Procedure

Prepared according to the method described in Example 5 from 2-(2-propenyloxy)-7-hydroxynaphthalene (1.27 g; J. Org. Chem., (1981) 46, 4988), sodium hydride (60% dispersion in oil; 0.25 g) and (±)-3-(2-oxiranylethyl)pyridine (1.0 g) in dimethylformamide (20 ml) at room temperature to yield the title compound as an oil (0.410 g).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-eb7b7c80f81e4debb700d6ebed2b5020
Source dataset
uspto-grants-1999_11
Patent number
US05977105

Reaction notes

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