Water → HCID 67409224, compound

HRID 1403679Notes

Reaction equation

HRID 1403679 reaction equation
[CH3:1][O:2][CH:3]1[CH:7]([OH:8])[CH2:6][CH2:5][O:4]1.[H-].[Na+].[CH2:11]([O:18][CH2:19][CH2:20]O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.O>CN(C=O)C>[CH2:11]([O:18][CH2:19][CH2:20][O:8][CH:7]1[CH2:6][CH2:5][O:4][CH:3]1[O:2][CH3:1])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 121412-(Benzyloxy) ethanolHCID 24758Sodium hydrideHCID 14804729HCID 14804729, compound

Product 1

HCID 67409224HCID 67409224, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2-methoxy-tetrahydro-furan-3-ol in DMF 200 mL was added sodium hydride in small portions with stirring at 0° C. for 2 hrs, then 2-Benzyloxy-ethanol was added from the dropping funnel over a period of 1 hour, the resulting mixture was stirred at 25° C. for 15 hrs, it was poured into 400 mL water, EtOAC (1 L) were added and separated. The organic layer was washed with sat. NaHCO3 (500 mL), dried over Na2SO4, filtered and concentrated, The residue was purified by column chromatography (PE:EA=5:1) to yield 10 g of 3-(2-Benzyloxy-ethoxy)-2-methoxy-tetrahydro-furan (oil).

Workup

  1. stirringthe resulting mixture was stirred at 25° C. for 15 hrs
  2. additionwere added
  3. customseparated
  4. washThe organic layer was washed with sat. NaHCO3 (500 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography (PE:EA=5:1)

Sources & evidence

ORD record
ord-a17b59da4e054d148f3c8467eb802ded
Source dataset
uspto-grants-2014_12
Patent number
US08912209B2

Reaction notes

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