Ethyl 3-(2-chloropyridin-5-yl)propionate → 3-(6-Chloropyridin-3-yl)propan-1-ol

HRID 53201Notes

Reaction equation

HRID 53201 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][C:16](OCC)=[O:17])=[CH:10][N:9]=1>C1COCC1>[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][OH:17])=[CH:10][N:9]=1

Participants

4

Reactant 2

HCID 19082020Ethyl 3-(2-chloropyridin-5-yl)propionateHCID 21226445Aluminium lithium hydride

Product 1

HCID 140715693-(6-Chloropyridin-3-yl)propan-1-olYield 97.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 0.2 g of LAH in 25 ml of dry THF at 0° C. under nitrogen was added a solution of 1.11 g (5.2 mmol) of ethyl 3-(2-chloropyridin-5-yl)-propionate in 5 ml of THF. The reaction mixture was kept at 3° C.-5° C. for 1 h and quenched with 0.2 ml of water, 0.2 ml of 10% NaOH, and 0.6 ml of water successively. The mixture was filtered through celite (washing with ether) and the filtrate was concentrated in vacuo to yield 0.87 g (theory) of 2-chloro-5-(3-hydroxypropyl)-pyridine as a yellow viscous oil (crude).

Workup

  1. customquenched with 0.2 ml of water, 0.2 ml of 10% NaOH, and 0.6 ml of water successively
  2. filtrationThe mixture was filtered through celite (washing with ether)
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-3b9640f65aad4037aff20306a49af7e5
Source dataset
uspto-grants-1997_04
Patent number
US05618821

Reaction notes

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