Tetrahydrofuran → (4-Chloro-3-methyl-2-pyridyl)-cyclopropyl-methanol

HRID 1061432Notes

Reaction equation

HRID 1061432 reaction equation
[CH:1]1(Br)[CH2:3][CH2:2]1.[Mg].[CH:6]1(Br)[CH2:8][CH2:7]1.[Mg].[Cl-:11].[NH4+:12].[CH2:13]1[CH2:17][O:16][CH2:15][CH2:14]1>>[Cl:11][C:8]1[CH:6]=[CH:7][N:12]=[C:1]([CH:15]([CH:14]2[CH2:13][CH2:17]2)[OH:16])[C:3]=1[CH3:2]

Participants

6

Reactant 5

HCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 78037BromocyclopropaneHCID 5462224MagnesiumHCID 66589449Magnesium cyclopropyl bromide

Product 1

HCID 12071707(4-Chloro-3-methyl-2-pyridyl)-cyclopropyl-methanol

Procedure

150 ml of a THF solution of 19.30 g of (4-chloro-3-methylpyridine)-2-carbardehyde (VIII) was dropped to 180 ml of THF solution of magnesium cyclopropyl bromide which was prepared from 14.9 ml of cyclopropyl bromide and 4.53 g of magnesium. The resulting mixture was stirred at a room temperature for 12 hours, and poured into saturated ammonium chloride solution and extracted with chloroform. The resulting organic layer was washed with saturated salt water and dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=3:1) to obtain 19.58 g of (4-chloro-3-methyl-2-pyridyl)cyclopropylmethane-1-ol (IX).

Workup

  1. extractionextracted with chloroform
  2. washThe resulting organic layer was washed with saturated salt water
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-7d36c6a0b210486eaef6be89feaf0da3
Source dataset
uspto-grants-2003_02
Patent number
US06525066B2

Reaction notes

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