Trityl chloride → HCID 10698078, compound

HRID 1501892Notes

Reaction equation

HRID 1501892 reaction equation
[CH2:1]([O:17][CH2:18][C@H: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.C(N(CC)CC)C>O1CCCC1.C(#N)C.CCCCCC>[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

7

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 10448487(S)-3-(Hexadecyloxy)propane-1,2-diol

Product 1

HCID 10698078HCID 10698078, compoundYield 87%

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

20 grams of (S)-1-hexadecyl-glycerol and 21.29 grams of triphenylchloromethane were dissolved in 369 ml dry tetrahydrofuran (THF) and 93 ml dry acetonitrile. 17.75 ml triethylamine was added and the reaction mixture was refluxed for 17 hours. The reaction mixture was cooled to room temperature, poured on ice (100 grams), transferred to a separatory funnel and extracted with methyl tert-butyl ether. The organic phase was washed consecutively with 200 ml water, twice with 200 ml dilute (1.5%) sulfuric acid, 200 ml water, 200 ml saturated aqueous sodium bicarbonate, and again with 200 ml water. The organic phase was dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure to give 36.86 grams of crude product as a residue. This residue was dissolved in hot hexane (200 ml) and the resulting solution was cooled at 4° C. overnight. The precipitated product was filtered, yielding 30.71 grams of (R)-1-hexadecyl-3-trityl-glycerol.

Workup

  1. temperaturethe reaction mixture was refluxed for 17 hours
  2. additionpoured on ice (100 grams)
  3. customtransferred to a separatory funnel
  4. extractionextracted with methyl tert-butyl ether
  5. washThe organic phase was washed consecutively with 200 ml water, twice with 200 ml
  6. additiondilute (1.5%) sulfuric acid, 200 ml water, 200 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. customto give 36.86 grams of crude product as a residue
  10. temperaturethe resulting solution was cooled at 4° C. overnight
  11. filtrationThe precipitated product was filtered

Sources & evidence

ORD record
ord-9c1afa3252fc4bfea56920453459eb5e
Source dataset
uspto-grants-2015_12
Patent number
US09206206B2

Reaction notes

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