Diethyl Ether → Acetic acid 4-(4-methoxy-but-1-ynyl)pyridin-3-yl ester

HRID 252369Notes

Reaction equation

HRID 252369 reaction equation
I[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[O:8][C:9](=[O:11])[CH3:10].[CH3:12][O:13][CH2:14][CH2:15][C:16]#[CH:17].C(OCC)C>O1CCCC1>[CH3:12][O:13][CH2:14][CH2:15][C:16]#[C:17][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[O:8][C:9](=[O:11])[CH3:10]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 5421524-Methoxybut-1-yneHCID 68782160Acetic acid 4-iodo-pyridin-3-yl ester

Product 1

HCID 66887632Acetic acid 4-(4-methoxy-but-1-ynyl)pyridin-3-yl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

0.95 mmol Palladium dichloride bis-triphenylphoshine and 0.97 mmol cupric chloride are dissolved in 64 ml tetrahydrofuran under an argon atmosphere. A solution of 30 mmol acetic acid 4-iodo-pyridin-3-yl ester [289473-46-7] and 38 mmol 4-methoxy-but-1-yne [36678-08-7] in 50 ml tetrahydrofuran is added in one portion and the reaction mixture is stirred at room temperature for 1 hour. 300 ml of diethyl ether are added and the precipitate is filtered off. The filtrate is washed successively with saturated, aqueous ammonium chloride solution (3×), water (2×) and brine. The organic layer is dried over sodium sulphate, filtered and concentrated. The title compound is obtained from the residue by means of flash chromatography (SiO2 60F) and identified based on its Rf value.

Workup

  1. filtrationthe precipitate is filtered off
  2. washThe filtrate is washed successively with saturated, aqueous ammonium chloride solution (3×), water (2×) and brine
  3. dry with materialThe organic layer is dried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0c5c89009df34f039b164c2fc3bcb7dd
Source dataset
uspto-grants-2011_01
Patent number
US07868036B2

Reaction notes

Loading…