1-Hexanol → HCID 13603721, compound

HRID 651910Notes

Reaction equation

HRID 651910 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:11]2[C:12](=[O:23])[C:13]([N:18]3[CH:22]=[CH:21][CH:20]=[N:19]3)=[CH:14][N:15]([CH3:17])[CH:16]=2)[CH:8]=[CH:9][CH:10]=1)=[O:4].[CH2:24](O)[CH2:25][CH2:26][CH2:27][CH2:28]C>O1CCCC1.[Ti]>[CH2:1]([O:2][C:3]([C:5]1[CH:6]=[C:7]([C:11]2[C:12](=[O:23])[C:13]([N:18]3[CH:22]=[CH:21][CH:20]=[N:19]3)=[CH:14][N:15]([CH3:17])[CH:16]=2)[CH:8]=[CH:9][CH:10]=1)=[O:4])[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

5

Reactant 2

HCID 81031-HexanolHCID 13603719HCID 13603719, compound

Product 1

HCID 13603721HCID 13603721, compoundYield 21.4%

Reagents, catalysts & solvents 2

HCID 23963TitaniumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

5 g (0.016 mole) of 5-(3-methoxycarbonylphenyl)-1-methyl-3-(pyrazol-1-yl)-4-pyridone and 16.32 g (0.16 mole) of n-hexanol are extracted under reflux together with 3.64 g (0.016 mole) of titanium tetraethylate in 50 ml of absolute tetrahydrofuran for 12 hours over a Soxhlet extractor filled with 4 Å zeolite. The reaction mixture is concentrated to dryness, the residue is taken up in water and the mixture is extracted three times with methylene chloride; the combined organic phases are dried over sodium sulphate and concentrated in vacuo. The oil which remains is purified chromatographically over a silica gel column (eluant: cyclohexane/ethyl acetate 1:1) and the product is crystallized from ether. 1.3 g (21.4% of theory) of 5-(3-n-hexyloxycarbonylphenyl)-1-methyl-3-(pyrazol-1-yl)-4-pyridone of melting point 96°-97° C. are obtained.

Workup

  1. concentrationThe reaction mixture is concentrated to dryness
  2. extractionthe mixture is extracted three times with methylene chloride
  3. dry with materialthe combined organic phases are dried over sodium sulphate
  4. concentrationconcentrated in vacuo
  5. customThe oil which remains is purified chromatographically over a silica gel column (eluant: cyclohexane/ethyl acetate 1:1)
  6. customthe product is crystallized from ether

Sources & evidence

ORD record
ord-2ee193c7f93e440cb2337d446fcf9071
Source dataset
uspto-grants-1987_06
Patent number
US04670044

Reaction notes

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