1-Bromooctane → HCID 86648425, compound

HRID 2387412Notes

Reaction equation

HRID 2387412 reaction equation
[CH3:1][C:2]1([C:26]([OH:28])=[O:27])[O:7][CH2:6][CH:5]([CH2:8][CH2:9][CH2:10][CH2:11][O:12][N:13]=[C:14]([C:16]2[CH:25]=[CH:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=2)[CH3:15])[CH2:4][O:3]1.[CH2:29](Br)[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:29]([O:27][C:26]([C:2]1([CH3:1])[O:3][CH2:4][CH:5]([CH2:8][CH2:9][CH2:10][CH2:11][O:12][N:13]=[C:14]([C:16]2[CH:25]=[CH:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=2)[CH3:15])[CH2:6][O:7]1)=[O:28])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]

Participants

5

Reactant 3

HCID 81401-BromooctaneHCID 11430Potassium CarbonateHCID 73314213HCID 73314213, compound

Product 1

HCID 86648425HCID 86648425, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2-Methyl-5-[4-(1-naphthalen-2-yl-ethylideneaminooxy)-butyl]-[1,3]dioxane-2-carboxylic acid (prepared as per example 63) (0.9 g), n-octyl bromide (0.6 mL) and potassium carbonate (0.64 g) in anhydrous dimethyl formamide (10 mL) was stirred at 60° C. for about 8 hours in an inert atmosphere. The reaction mixture was cooled to ambient temperature, poured into ice cold water and extracted with ethyl acetate. The combined organic extract was washed with water, brine solution, dried over sodium sulphate and evaporated under reduced pressure. Crude product was flash chromatographed over silica gel 8% ethyl acetate in petroleum ether as eluent to obtain 1 g of pure product.

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. additionpoured into ice cold water
  3. extractionextracted with ethyl acetate
  4. extractionThe combined organic extract
  5. washwas washed with water, brine solution
  6. dry with materialdried over sodium sulphate
  7. customevaporated under reduced pressure
  8. customchromatographed over silica gel 8% ethyl acetate in petroleum ether as eluent

Sources & evidence

ORD record
ord-b8d694de5ec5430183092118db6b4f80
Source dataset
uspto-grants-2012_09
Patent number
US08268867B2

Reaction notes

Loading…