Water → 1-(2,5-Dimethoxy-3,4,6-trimethylphenyl)-1-(3-pyridyl)heptanol

HRID 484023Notes

Reaction equation

HRID 484023 reaction equation
[Mg].Br[C:3]1[C:8]([CH3:9])=[C:7]([O:10][CH3:11])[C:6]([CH3:12])=[C:5]([CH3:13])[C:4]=1[O:14][CH3:15].[C:16]([C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1)(=[O:23])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].O>O1CCCC1>[CH3:15][O:14][C:4]1[C:5]([CH3:13])=[C:6]([CH3:12])[C:7]([O:10][CH3:11])=[C:8]([CH3:9])[C:3]=1[C:16]([C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1)([OH:23])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

6

Reactant 4

HCID 962WaterHCID 2227091-(Pyridin-3-yl)heptan-1-oneHCID 2973651-Bromo-2,5-dimethoxy-3,4,6-trimethylbenzeneHCID 5462224Magnesium

Product 1

HCID 145762641-(2,5-Dimethoxy-3,4,6-trimethylphenyl)-1-(3-pyridyl)heptanolYield 39.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A Grignard reagent was prepared from 693 mg (28.3 g atom) of magnesium, 7.6 g (29.3 mmol) of 1-bromo-2,5-dimethoxy-3,4,6-trimethylbenzene and tetrahydrofuran at 65° C. and cooled to 0° C., to which a solution of 3.75 g (21.9 mmol) of 3-heptanoylpyridine in 10 ml of tetrahydrofuran was added dropwise. After completion of the addition, the reaction mixture was stirred at room temperature for 1 hour, to which water was added and extracted with ethyl acetate. The extract was washed with water, dried and concentrated. The residue was purified with silica gel column chromatography (isopropyl ether) and recrystallized from hexane, to give 3.2 g (39%) of 1-(2,5-dimethoxy-3,4,6-trimethylphenyl)-1-(3-pyridyl)heptanol. m.p. 109°-110° C.

Workup

  1. additionwas added dropwise
  2. additionAfter completion of the addition
  3. additionwas added
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with water
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was purified with silica gel column chromatography (isopropyl ether)
  9. customrecrystallized from hexane

Sources & evidence

ORD record
ord-31cd0ae4bb3946dfa0a90a495d74bfbe
Source dataset
uspto-grants-1993_07
Patent number
US05229385

Reaction notes

Loading…