Water → HCID 20037837, compound

HRID 1904670Notes

Reaction equation

HRID 1904670 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][OH:5].[H-].[Na+].Cl.Cl[CH2:10][C:11]1[CH:12]=[C:13]([CH:26]=[CH:27][CH:28]=1)[O:14][CH2:15][C:16]1[CH:25]=[CH:24][C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]=1.O>C1COCC1>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:10][C:11]1[CH:12]=[C:13]([CH:26]=[CH:27][CH:28]=1)[O:14][CH2:15][C:16]1[CH:25]=[CH:24][C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 80192-MethoxyethanolHCID 24758Sodium hydrideHCID 145017072-(3-Chloromethylphenoxymethyl)quinoline hydrochloride

Product 1

HCID 20037837HCID 20037837, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

1.1 g (0.015 mol) of 2-methoxyethanol was dissolved in 50 ml THF. To this solution 1.5 g (0.03 mol, 50% oil dispersion) NaH, (0.015 mol) 2-(3-chloromethylphenoxymethyl)quinoline hydrochloride, was added slowly. After the addition was completed, the mixture was heated at 70° C. bath temperature for overnight. The reaction mixture was poured into water and extracted with ether. The ether extract was washed with water, dried and concentrated to dryness under reduced pressure. The residue was passed through a silica gel column using hexane/ethylacetate (3:1) as eluent. Evaporation of eluent gave light yellow oil (1.1 g).

Workup

  1. additionAfter the addition
  2. extractionextracted with ether
  3. extractionThe ether extract
  4. washwas washed with water
  5. customdried
  6. concentrationconcentrated to dryness under reduced pressure
  7. customEvaporation of eluent

Sources & evidence

ORD record
ord-b9ba34ccf7c04b23a779a6c48ed3e79d
Source dataset
uspto-grants-1989_06
Patent number
US04839369

Reaction notes

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