Triethyl Citrate → HCID 86688829, compound

HRID 2275519Notes

Reaction equation

HRID 2275519 reaction equation
[C:1]([O:17][CH2:18][CH3:19])(=[O:16])[CH2:2][C:3]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])([C:5]([O:7][CH2:8][CH3:9])=[O:6])[OH:4].[H-].[Na+].[C:22](Cl)(=O)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]/[CH:30]=[CH:31]\[CH2:32][CH2:33][CH2:34]CCCCC>O1CCCC1>[C:11]([OH:13])(=[O:12])[CH2:10][CH2:3][CH2:2][CH2:1][CH2:22][CH2:23][CH2:24]/[CH:25]=[CH:26]\[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34].[C:11]([O:13][CH2:14][CH3:15])(=[O:12])[CH2:10][C:3]([CH2:2][C:1]([O:17][CH2:18][CH3:19])=[O:16])([C:5]([O:7][CH2:8][CH3:9])=[O:6])[OH:4]

Participants

5

Reactant 3

HCID 6506Triethyl CitrateHCID 24758Sodium hydrideHCID 5364783Oleoyl chloride

Product 1

HCID 86688829HCID 86688829, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of triethyl citrate (0.87 g, 1 equivalent) in tetrahydrofuran (THF) was added to a solution of sodium hydride (0.2 g, 1.5 equivalents) in THF at 0° C. and stirred at 0° C. for 1 hour. Then oleoyl chloride (0.87 g, 1 equivalent) was added and stirred for 1 hour at 0° C. under nitrogen atmosphere. The mixture was stirred at 25-30° C. for 8 hours. Thin layer chromatography analysis indicated that the reaction was complete. The mixture was quenched with cold water and extracted with ethyl acetate. The ethyl acetate phase was washed with sodium bicarbonate solution (10%) followed by water and then brine solution. The resulting mixture was dried over sodium sulphate and concentrated to obtain a crude product. Purified product was obtained from the crude product by column chromatography using 10% petroleum ether in ethyl acetate as eluent. Yield of product was 0.6 g.

Workup

  1. stirringstirred for 1 hour at 0° C. under nitrogen atmosphere
  2. stirringThe mixture was stirred at 25-30° C. for 8 hours
  3. customThe mixture was quenched with cold water
  4. extractionextracted with ethyl acetate
  5. washThe ethyl acetate phase was washed with sodium bicarbonate solution (10%)
  6. dry with materialThe resulting mixture was dried over sodium sulphate
  7. concentrationconcentrated
  8. customto obtain a crude product

Sources & evidence

ORD record
ord-880b5d2ccbbc4396a843d167bab9d4a1
Source dataset
uspto-grants-2015_09
Patent number
US09127232B2

Reaction notes

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