Cesium carbonate → HCID 17975811, compound

HRID 2108843Notes

Reaction equation

HRID 2108843 reaction equation
[OH:1][C:2]1[C:3](=[O:16])[CH:4]=[C:5]([CH2:8][O:9][CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][O:11]2)[O:6][CH:7]=1.[C:17]([O-])([O-])=O.[Cs+].[Cs+].BrC[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][Br:30]>CN(C=O)C>[Br:30][CH:29]([CH3:17])[CH2:28][CH2:27][CH2:26][CH2:25][O:1][C:2]1[C:3](=[O:16])[CH:4]=[C:5]([CH2:8][O:9][CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][O:11]2)[O:6][CH:7]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 123681,6-DibromohexaneHCID 137117895-Hydroxy-2-{[(oxan-2-yl)oxy]methyl}-4H-pyran-4-one

Product 1

HCID 17975811HCID 17975811, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

5-Hydroxy-2-(tetrahydro-pyran-2-yloxymethyl)-4H-pyran-4-one (1.50 g, 6.60 mmol) was charged in a 30 mL sealed tube equipped with a magnetic stirrer and under inert atmosphere. Anhydrous DMF (10 mL), Cs2CO3 (2.30 g, 7.00 mmol) and 1,6-dibromo-hexane (3.20 g, 13.30 mmol) were successively added. The reaction mixture was stirred 2 h at 60° C. After evaporation of DMF, the crude compound was purified by column chromatography (SiO2; CH2Cl2:EtOAc=8:2) to give after evaporation 5-(6-bromo-hexyloxy)-2-(tetrahydro-pyran-2-yloxymethyl)-4H-pyran-4-one 3 as an oil (190 mg, 52% yield).

Workup

  1. customsealed tube
  2. customequipped with a magnetic stirrer and under inert atmosphere
  3. customAfter evaporation of DMF
  4. customthe crude compound was purified by column chromatography (SiO2; CH2Cl2:EtOAc=8:2)
  5. customto give

Sources & evidence

ORD record
ord-e284b0d15c4942e0979f08a9655100c1
Source dataset
uspto-grants-2009_04
Patent number
US07514432B2

Reaction notes

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