Sodium Acetate → HCID 21867058, compound

HRID 857088Notes

Reaction equation

HRID 857088 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][C:11]#[C:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=1.[C:22]([O-:25])(=[O:24])[CH3:23].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C.O>[C:22]([O:25][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][C:11]#[C:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=1)(=[O:24])[CH3:23]

Participants

6

Reactant 2

HCID 517045Sodium AcetateHCID 218670991-{4-[(6-Bromohexyl)oxy]but-1-ynyl}-3-nitrobenzene

Product 1

HCID 21867058HCID 21867058, compoundYield 75.6%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 1-{4-[(6-bromohexyl)oxy]but-1-ynyl}-3-nitrobenzene (4.18 g), sodium acetate (9.68 g), tetrabutylammonium bromide (384 mg) in DMF (15 ml) and water (10 ml) was heated to 75° C. for 6 h. The mixture was then allowed to cool to 20° C. and then extracted with Et2O. The organic solution was concentrated and purified by chromatography on a Biotage (40 g) eluting with Et2O-petroleum ether(1:19 increasing to 1:1) to give the title compound (2.973 g). LCMS RT=3.84 min.

Workup

  1. temperatureto cool to 20° C.
  2. extractionextracted with Et2O
  3. concentrationThe organic solution was concentrated
  4. custompurified by chromatography on a Biotage (40 g)
  5. washeluting with Et2O-petroleum ether(1:19 increasing to 1:1)

Sources & evidence

ORD record
ord-a953688cfe044b28be5e4ac8f1644c0a
Source dataset
uspto-grants-2006_12
Patent number
US07144908B2

Reaction notes

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