Potassium Carbonate → [4-(3-Chloropropoxy)-3-methylpyridin-2-yl]methanol

HRID 1637617Notes

Reaction equation

HRID 1637617 reaction equation
C([O:4][CH2:5][C:6]1[C:11]([CH3:12])=[C:10]([O:13][CH2:14][CH2:15][CH2:16][Cl:17])[CH:9]=[CH:8][N:7]=1)(=O)C.C(=O)([O-])[O-].[K+].[K+]>CO>[Cl:17][CH2:16][CH2:15][CH2:14][O:13][C:10]1[CH:9]=[CH:8][N:7]=[C:6]([CH2:5][OH:4])[C:11]=1[CH3:12]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 187994054-(3-Chloropropoxy)-3-methylpyridin-2-ylmethyl acetate

Product 1

HCID 18799386[4-(3-Chloropropoxy)-3-methylpyridin-2-yl]methanolYield 58%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2.7 g (10.4 mmol) of the oil from stage b) in 25 ml of methanol is treated with 1.5 g (20.8 mmol) of potassium carbonate and stirred at room temperature for 4 h. The salts are then filtered off and the filtrate is concentrated. The residue is purified by chromatography on silica gel (eluent: ethyl acetate/methanol/ammonia=19:1:0.4). 1.3 g (57%) of the title compound are isolated as a colorless oil which partially crystallizes after standing for a relatively long time. This product is employed directly for the further reaction (Example 15) without additional purification.

Workup

  1. filtrationThe salts are then filtered off
  2. concentrationthe filtrate is concentrated
  3. customThe residue is purified by chromatography on silica gel (eluent: ethyl acetate/methanol/ammonia=19:1:0.4)

Sources & evidence

ORD record
ord-0e286d28c3d04fce92001472064d4599
Source dataset
uspto-grants-2000_03
Patent number
US06043242

Reaction notes

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