Dimethoxymethane → HCID 14512958, compound

HRID 1165760Notes

Reaction equation

HRID 1165760 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][OH:9])[CH:5]=[CH:4][N:3]=1.[CH3:10][O:11][CH2:12]OC.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][O:9][CH2:10][O:11][CH3:12])[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 8020DimethoxymethaneHCID 521998p-Toluenesulfonic acid monohydrateHCID 14512957(2-Bromopyridin-4-yl)methanol

Product 1

HCID 14512958HCID 14512958, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

70 ml of 2-bromo-4-pyridinemethanol, 70 ml of dimethoxymethane and 2.15 g of p-toluenesulfonic acid monohydrate were suspended in 300 ml of benzene. The suspension was passed through a Soxhlet extractor containing 25 g of 3 Å molecular sieves, and refluxed for 20 hours. After cooling, the reaction mixture was washed with a saturated aqueous solution of sodium hydrogen carbonate and water, dried, and concentrated under reduced pressure. The residue was distilled to give 13.2 g (yield 50%) of 2-bromo-4-(methoxymethoxymethyl)pyridine.

Workup

  1. additioncontaining 25 g of 3 Å molecular sieves
  2. temperaturerefluxed for 20 hours
  3. temperatureAfter cooling
  4. washthe reaction mixture was washed with a saturated aqueous solution of sodium hydrogen carbonate and water
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. distillationThe residue was distilled

Sources & evidence

ORD record
ord-39c129c0286a4866882adbedc31cd67e
Source dataset
uspto-grants-1990_03
Patent number
US04912101

Reaction notes

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