Dimethoxymethane → HCID 18932635, compound

HRID 1452403Notes

Reaction equation

HRID 1452403 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[CH:11]([CH2:14][CH3:15])[CH2:12][OH:13].[CH3:16]OCOC>CCOCC>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[C:5]2[C:4]=1[CH:11]([CH2:14][CH3:15])[CH2:12][O:13][CH2:16]2

Participants

4

Reactant 2

HCID 8020DimethoxymethaneHCID 18932640HCID 18932640, compound

Product 1

HCID 18932635HCID 18932635, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Under argon atmosphere, the product from step 2 herein, 2.74 g (13.03 mmol) was dissolved in 55 ml of dry ether. Dimethoxy methane 1.65 ml (19.55 mmol) and boron trifluoro etherate 4.9 ml (39.09 mmol) were then added to this solution. The obtained reaction mixture was left stirring overnight. The reaction mixture was quenched using aqueous NaHCO3 and extractions were done using ether. The combined organic extracts were dried over Na2SO4, filtered, and the solvent was removed. The residue was purified by flash chromatography using hexanes-ethyl acetate (80:20) and (70:30) as eluent. The isolated titled product was a white solid (1.56 g; 54%).

Workup

  1. customThe obtained reaction mixture
  2. waitwas left
  3. customThe reaction mixture was quenched
  4. extractionNaHCO3 and extractions
  5. dry with materialThe combined organic extracts were dried over Na2SO4
  6. filtrationfiltered
  7. customthe solvent was removed
  8. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-e03ffa8d88a14b149167b5d5eb1990a5
Source dataset
uspto-grants-1997_02
Patent number
US05606037

Reaction notes

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