Potassium Carbonate → HCID 131731339, compound

HRID 2369277Notes

Reaction equation

HRID 2369277 reaction equation
[CH3:1][C:2]([CH2:10][CH2:11][CH2:12][CH:13]([CH3:25])[CH2:14][CH2:15][CH2:16][CH:17]([CH3:24])[CH2:18][CH2:19][CH2:20][CH:21]([CH3:23])[CH3:22])=[CH:3][CH2:4][CH2:5][C:6]([O:8][CH3:9])=[O:7].[CH2:26]([OH:35])[C@@H:27]([C@H:29]([C@@H:31](CO)[OH:32])[OH:30])[OH:28].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:1][C:2]([CH2:10][CH2:11][CH2:12][CH:13]([CH3:25])[CH2:14][CH2:15][CH2:16][CH:17]([CH3:24])[CH2:18][CH2:19][CH2:20][CH:21]([CH3:23])[CH3:22])=[CH:3][CH2:4][CH2:5][C:6]([O:8][CH2:9][C@@H:26]([C@H:27]([C@@H:29]([CH2:31][OH:32])[OH:30])[OH:28])[OH:35])=[O:7]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 54269534HCID 54269534, compoundHCID 178418489HCID 178418489, compound

Product 1

HCID 131731339HCID 131731339, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

1.0 g (2.8 mmol) of methyl 5,9,13,17-tetramethyloctadec-4-enoate was slowly added dropwise to a solution of 0.86 g (2.8 mmol) of xylitol and 0.78 g (5.7 mmol) of potassium carbonate in dry N,N-dimethylformamide (2.5 mL) at 80° C. After the reaction mixture was stirred at 100° C. for 24 hours, the potassium carbonate was separated by filtration. The resulting solution was diluted with t-butylmethylether, and washed with water, 1M hydrochloric acid, saturated sodium bicarbonate aqueous solution, and saturated brine, successively, and dried over magnesium sulfate. After filtration, the filtrate was concentrated, and the resulting residue was purified by silica gel column chromatography (methanol/methylene chloride mixture) to obtain 146 mg of the title compound (12% yield) as a colorless viscous product.

Workup

  1. customthe potassium carbonate was separated by filtration
  2. additionThe resulting solution was diluted with t-butylmethylether
  3. washwashed with water, 1M hydrochloric acid, saturated sodium bicarbonate aqueous solution, and saturated brine
  4. dry with materialsuccessively, and dried over magnesium sulfate
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated
  7. customthe resulting residue was purified by silica gel column chromatography (methanol/methylene chloride mixture)

Sources & evidence

ORD record
ord-fa92874107f34c5081390a407536641e
Source dataset
uspto-grants-2014_04
Patent number
US08703922B2

Reaction notes

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