Hydrochloric Acid → HCID 13793774, compound

HRID 1654125Notes

Reaction equation

HRID 1654125 reaction equation
[O:1]1[C:5]([CH2:6][OH:7])=[CH:4][CH:3]=[C:2]1[CH2:8][OH:9].[H-].[Na+].S(OC)(O[CH3:16])(=O)=O.Cl>O1CCCC1.CN(C)C=O>[CH3:16][O:7][CH2:6][C:5]1[O:1][C:2]([CH2:8][OH:9])=[CH:3][CH:4]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 746632,5-Furandimethanol

Product 1

HCID 13793774HCID 13793774, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

6.4 g of 2,5-furandimethanol were dissolved at 20° C. in 120 ml of tetrahydrofuran and 2.4 g of sodium hydride were added over 30 minutes. The mixture was stirred for 2 hours and 60 ml of dimethylformamide and 4.7 ml of dimethyl sulfate were added. The mixture was stirred for 16 hours at 20° C., poured into ice-cold water and acidified with hydrochloric acid. The mixture was extracted with isopropyl ether and the extract was washed with water and dried. The solvent was evaporated and the residue was chromatographed on silica (eluent: 5/5 hexane/ethyl acetate) to obtain 2.97 g of the expected product.

Workup

  1. stirringThe mixture was stirred for 16 hours at 20° C.
  2. additionpoured into ice-cold water
  3. extractionThe mixture was extracted with isopropyl ether
  4. washthe extract was washed with water
  5. customdried
  6. customThe solvent was evaporated
  7. customthe residue was chromatographed on silica (eluent: 5/5 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-d6c207d6c54f455b81226bc0b87ee325
Source dataset
uspto-grants-1995_04
Patent number
US05405865

Reaction notes

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