1,5-Dibromopentane → HCID 12149143, compound

HRID 2108841Notes

Reaction equation

HRID 2108841 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([O-])([O-])=O.[Cs+].[Cs+].[Br:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]Br>CN(C=O)C>[Br:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][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 81001,5-DibromopentaneHCID 10796Cesium carbonateHCID 137117895-Hydroxy-2-{[(oxan-2-yl)oxy]methyl}-4H-pyran-4-one

Product 1

HCID 12149143HCID 12149143, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
92.5 °C

Procedure

The compound was prepared according to example 11 using 5-hydroxy-2-(tetrahydro-pyran-2-yloxymethyl)-4H-pyran-4-one (3.5 g, 15.5 mmol) in 20 mL of DMF, Cs2CO3 (5.04 g, 15.5 mmol) and 1,5-dibromopentane (8.8 g, 36.7 mmol). The sealed tube was heated at 90-95° C. for 1 h 40. A white solid 1 was obtained (5.30 g, 91% yield).

Workup

  1. customThe compound was prepared

Sources & evidence

ORD record
ord-7f6387d1bcbf48ed93c2fc3a4e09ea20
Source dataset
uspto-grants-2009_04
Patent number
US07514432B2

Reaction notes

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