Acetonitrile → HCID 10698078, compound

HRID 1464916Notes

Reaction equation

HRID 1464916 reaction equation
[CH2:1]([O:17][CH2:18][CH:19]([CH2:21][OH:22])[OH:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[C:23]1([C:29]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)Cl)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.O1CCCC1.C(#N)C>C(N(CC)CC)C>[CH2:1]([O:17][CH2:18][C@H:19]([CH2:21][O:22][C:29]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[OH:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 6456Trityl chlorideHCID 8028TetrahydrofuranHCID 727331-O-Hexadecylglycerol

Product 1

HCID 10698078HCID 10698078, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

40 grams of 1-hexadecyl-glycerol and 43 grams triphenylchloromethane were added to a mixture of 500 ml dry tetrahydrofuran and 130 ml dry acetonitrile. 35 ml of dry triethylamine was added, and the reaction mixture was refluxed for 17 hours. The reaction mixture was then cooled to room temperature, poured on ice (1 kilogram) and extracted thrice with 250 ml diethyl ether. The organic phase was washed consecutively with 100 ml water, 100 ml dilute (1.5%) sulfuric acid, 100 ml water, 100 ml concentrated aqueous sodium bicarbonate and again with 100 ml water. The obtained organic phase was dried over anhydrous sodium sulfate and the solvent was thereafter removed under reduced pressure. The residue was dissolved in 200 ml ethyl acetate and the resulting solution was cooled at −20° C. overnight. The mixture was then centrifuged at −5° C. and the mother liquid solution was poured off. The solid was dissolved in hexane and refrigerated overnight at 5° C. Filtration of the precipitate yielded pure 1-hexadecyl-3-trityl-sn-glycerol.

Workup

  1. temperaturethe reaction mixture was refluxed for 17 hours
  2. additionpoured on ice (1 kilogram)
  3. extractionextracted thrice with 250 ml diethyl ether
  4. washThe organic phase was washed consecutively with 100 ml water, 100 ml
  5. additiondilute (1.5%) sulfuric acid, 100 ml water, 100 ml concentrated aqueous sodium bicarbonate
  6. dry with materialThe obtained organic phase was dried over anhydrous sodium sulfate
  7. customthe solvent was thereafter removed under reduced pressure
  8. dissolutionThe residue was dissolved in 200 ml ethyl acetate
  9. temperaturethe resulting solution was cooled at −20° C. overnight
  10. customwas then centrifuged at −5° C.
  11. additionthe mother liquid solution was poured off
  12. dissolutionThe solid was dissolved in hexane and refrigerated overnight at 5° C
  13. filtrationFiltration of the precipitate

Sources & evidence

ORD record
ord-8a52d0998624438298eccce1694258fb
Source dataset
uspto-grants-2015_04
Patent number
US08999960B2

Reaction notes

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