Acetonitrile → HCID 67230477, compound

HRID 1501897Notes

Reaction equation

HRID 1501897 reaction equation
[CH2:1]([O:9][CH2:10][C@H:11]([CH2:13][OH:14])[OH:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[C:15]1([C:21]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)Cl)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C1COCC1.C(#N)C>C(N(CC)CC)C>[CH2:1]([O:9][CH2:10][C@H:11]([CH2:13][O:14][C:21]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[OH:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 6456Trityl chlorideHCID 8028TetrahydrofuranHCID 15956913HCID 15956913, compound

Product 1

HCID 67230477HCID 67230477, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

34 grams of (S)-1-octyl-glycerol and 61 grams of triphenylchloromethane were added to a mixture of 500 ml of dry THF and 130 ml of dry acetonitrile. 46 ml of dry triethylamine was added, and the reaction mixture was refluxed for 17 hours. The reaction mixture was then cooled to room temperature and poured on ice (1 kilogram). The mixture was transferred to a separatory funnel and extracted thrice with 200 ml diethyl ether. The organic phase was washed consecutively with 150 ml water, twice with 100 ml dilute (1.5%) H2SO4, 200 ml water, 200 ml concentrated aqueous sodium bicarbonate, and again with 200 ml water. The solution was then dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure. The obtained residue, 80 grams of a brown oil, was dissolved in 500 ml hot hexane and kept at a temperature of 4° C. overnight. The precipitate was filtered off and the solvent from the filtrate was removed under reduced pressure. The obtained residue was purified by chromatography on silica gel. The resulting pure (R)-1-octyl-3-trityl-glycerol was eluted by mixtures of chloroform with 10% hexane, chloroform with 5% hexane, followed by chloroform with ethyl acetate (5% and 10%). The yield was 73%.

Workup

  1. temperaturethe reaction mixture was refluxed for 17 hours
  2. additionpoured on ice (1 kilogram)
  3. customThe mixture was transferred to a separatory funnel
  4. extractionextracted thrice with 200 ml diethyl ether
  5. washThe organic phase was washed consecutively with 150 ml water, twice with 100 ml
  6. additiondilute (1.5%) H2SO4, 200 ml water, 200 ml concentrated aqueous sodium bicarbonate
  7. dry with materialThe solution was then dried over anhydrous Na2SO4
  8. customthe solvent was removed under reduced pressure
  9. dissolutionThe obtained residue, 80 grams of a brown oil, was dissolved in 500 ml hot hexane
  10. customkept at a temperature of 4° C. overnight
  11. filtrationThe precipitate was filtered off
  12. customthe solvent from the filtrate was removed under reduced pressure
  13. customThe obtained residue was purified by chromatography on silica gel
  14. washThe resulting pure (R)-1-octyl-3-trityl-glycerol was eluted by mixtures of chloroform with 10% hexane, chloroform with 5% hexane

Sources & evidence

ORD record
ord-3307d32d36c34dfabbde03b0b26ed3c1
Source dataset
uspto-grants-2015_12
Patent number
US09206206B2

Reaction notes

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