Dimethylformamide → HCID 21263600, compound

HRID 566842Notes

Reaction equation

HRID 566842 reaction equation
CN(C)C=O.[CH3:6][C:7]([CH3:12])([CH2:10][OH:11])[CH2:8][OH:9].[H-].[Na+].Br[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]>O>[CH3:6][C:7]([CH3:12])([CH2:10][O:11][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH3:16])[CH2:8][OH:9]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 82181-BromooctadecaneHCID 24758Sodium hydrideHCID 31344Neopentyl glycol

Product 1

HCID 21263600HCID 21263600, compoundYield 54.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To an N,N-dimethylformamide solution (50 ml) containing 2.500 g of 2,2-dimethyl-1,3-propanediol was added an about 60% oil suspension containing 2.112 g of sodium hydride. After the reaction mixture was stirred under cooling with ice for 1 hour, 9.930 g of 1-bromo-octadecane was added dropwise thereto. After the reaction mixture was stirred at room temperature for 16.5 hours, water was added thereto and this mixture was extracted with hexane and ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (hexane:ethyl acetate=100:0 to 20:1). Thus, 4.700 g of the title compound was obtained in the form of a white solid.

Workup

  1. temperatureunder cooling with ice for 1 hour
  2. stirringAfter the reaction mixture was stirred at room temperature for 16.5 hours
  3. extractionthis mixture was extracted with hexane and ethyl acetate
  4. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c342f584cc8a43f3851cd0e797910bd0
Source dataset
uspto-grants-2001_01
Patent number
US06177067B1

Reaction notes

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