1,5-Dibromopentane → HCID 131727388, compound

HRID 2108844Notes

Reaction equation

HRID 2108844 reaction equation
[C:1]([SiH2:5][O:6][C:7]([CH3:17])([CH3:16])[C:8]1[O:9][CH:10]=[C:11]([OH:15])[C:12](=[O:14])[CH:13]=1)([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[Cs+].[Cs+].[Br:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]Br>CN(C=O)C>[Br:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][O:15][C:11]1[C:12](=[O:14])[CH:13]=[C:8]([C:7]([CH3:17])([CH3:16])[O:6][SiH2:5][C:1]([CH3:4])([CH3:2])[CH3:3])[O:9][CH:10]=1

Participants

5

Reactant 3

HCID 81001,5-DibromopentaneHCID 10796Cesium carbonateHCID 131727389HCID 131727389, compound

Product 1

HCID 131727388HCID 131727388, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

2-(tert-Butyl-dimethyl-silanyloxymethyl)-5-hydroxy-4H-pyran-4-one 6 (1.50 g, 5.85 mmol) was charged in a 100 mL round-bottomed flask equipped with a magnetic stirrer and under inert atmosphere. Anhydrous DMF (25 mL) and Cs2CO3 (2.10 g, 6.44 mmol) were successively added. After 5 min, 1,5-dibromopentane (2.39 mL, 17.55 mmol) was added via syringe at room temperature. The reaction mixture Novas heated at 50° C. for 3 h. After cooling and filtration DMF was removed in vacuo. The crude oil was purified by chromatography on silica using as eluent EtOAc:cyclohexane=20:80 then 30:70. After evaporation, 5-5-bromo-pentyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-4H-pyran-4-one 7 was obtained (1.25 g, 53% yield) as a white solid.

Workup

  1. customequipped with a magnetic stirrer and under inert atmosphere
  2. temperatureAfter cooling
  3. filtrationfiltration DMF
  4. customwas removed in vacuo
  5. customThe crude oil was purified by chromatography on silica using as eluent EtOAc
  6. customAfter evaporation, 5-5-bromo-pentyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-4H-pyran-4-one 7
  7. customwas obtained (1.25 g, 53% yield) as a white solid

Sources & evidence

ORD record
ord-ffe5c2f000f1481180969c0115ff3787
Source dataset
uspto-grants-2009_04
Patent number
US07514432B2

Reaction notes

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