Trityl chloride → HCID 86657045, compound

HRID 1501907Notes

Reaction equation

HRID 1501907 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]/[CH:9]=[CH: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.C(N(CC)CC)C>C1COCC1.C(#N)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]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

6

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 86657046HCID 86657046, compound

Product 1

HCID 86657045HCID 86657045, compoundYield 90.7%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

9.07 grams of 1-(cis-9-hexadecenyl)-glycerol was dissolved in a mixture of dry THF (160 ml) and dry acetonitrile (40 ml). 10.52 grams triphenylchloromethane and 10 ml triethylamine were added, and the reaction mixture was refluxed for 15 hours. The reaction mixture was cooled to room temperature, poured on ice (100 grams), transferred to a separatory funnel, and extracted thrice with 100 ml chloroform. The organic phase was washed consecutively with 100 ml water, 100 ml dilute (1.0%) sulfuric acid, 100 ml water, 100 ml saturated aqueous sodium bicarbonate, and again with 100 ml water. The organic phase was dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The obtained residue was dissolved in hot hexane (100 ml) and the resulting solution was cooled at 4° C. for 36 hours. Filtration of precipitated by-products and removal of solvent under reduced pressure yielded 14.57 grams of crude product. The crude product was purified by chromatography over silica gel (200 grams). 9.81 grams of pure 1-(cis-9-hexadecenyl)-3-trityl-sn-glycerol was eluted with chloroform. The yield was 61.1%.

Workup

  1. temperaturethe reaction mixture was refluxed for 15 hours
  2. additionpoured on ice (100 grams)
  3. customtransferred to a separatory funnel
  4. extractionextracted thrice with 100 ml chloroform
  5. washThe organic phase was washed consecutively with 100 ml water, 100 ml
  6. additiondilute (1.0%) sulfuric acid, 100 ml water, 100 ml saturated aqueous sodium bicarbonate
  7. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  8. customthe solvent was removed under reduced pressure
  9. dissolutionThe obtained residue was dissolved in hot hexane (100 ml)
  10. temperaturethe resulting solution was cooled at 4° C. for 36 hours
  11. filtrationFiltration of precipitated by-products and removal of solvent under reduced pressure

Sources & evidence

ORD record
ord-62db4a0ec064463faeb358d547ad6b33
Source dataset
uspto-grants-2015_12
Patent number
US09206206B2

Reaction notes

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