Tetrahydrofuran → HCID 14501719, compound

HRID 1904668Notes

Reaction equation

HRID 1904668 reaction equation
[O:1]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.Cl[CH2:18][C:19]1[CH:28]=[CH:27][C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]=1.[OH-].[Na+].C1COCC1>CN(C=O)C>[O:1]([CH2:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][CH2:18][C:19]2[CH:28]=[CH:27][C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[N:20]=2)=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 3161774-(phenoxymethyl)phenolHCID 30838232-(Chloromethyl)quinoline hydrochloride

Product 1

HCID 14501719HCID 14501719, compoundYield 23.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5.0 g (0.025 mol) 4-phenoxymethylphenol, 5.35 g (0.025 mol) 2-chloromethylquinoline hydrochloride and 30 ml (2N, NaOH) in 50 ml DMF and 100 ml THF was stirred at 60° C. bath temperature for a period of 3 hours. The reaction mixture was poured into wast and extracted with ether. The ether extract was washed with water, dried and concentrated to dryness to obtain solid. Recrystallization from acetonitrile yielded (2.0 g) product, m.p. 100°-111° C.

Workup

  1. additionThe reaction mixture was poured into wast
  2. extractionextracted with ether
  3. extractionThe ether extract
  4. washwas washed with water
  5. customdried
  6. concentrationconcentrated to dryness
  7. customto obtain solid
  8. customRecrystallization from acetonitrile

Sources & evidence

ORD record
ord-422986c63025470283f1400f0702c163
Source dataset
uspto-grants-1989_06
Patent number
US04839369

Reaction notes

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