Trityl chloride → HCID 10698078, compound

HRID 1501905Notes

Reaction equation

HRID 1501905 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>[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 3

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

Product 1

HCID 10698078HCID 10698078, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 35.3 grams of 1-hexadecyl-sn-glycerol, 37.3 grams of triphenylchloromethane and 22.44 grams of dry triethylamine in a mixture of 470 ml dry tetrahydrofuran and 120 ml dry acetonitrile was refluxed for 15 hours under a nitrogen atmosphere. After cooling to room temperature the reaction mixture was filtered. The filtrate poured on ice (500 grams) and then extracted thrice with 200 ml chloroform. The organic phase was washed successively with 500 ml water, 500 ml of 0.15 N HCl, 500 ml saturated aqueous NaHCO3, and again with water. The extract was dried over Na2SO4 and the solvent was removed under reduced pressure. The obtained yellow residue was dissolved in 500 ml warm hexane and the obtained clear solution was refrigerated (5±3° C.) overnight. During this time, precipitation occurred. After filtration of the precipitate, the solvent from the filtrate was removed under reduced pressure, yielding 58.3 grams of 1-hexadecyl-3-trityl-sn-glycerol. The yield was 95%.

Workup

  1. temperaturewas refluxed for 15 hours under a nitrogen atmosphere
  2. filtrationwas filtered
  3. additionThe filtrate poured on ice (500 grams)
  4. extractionextracted thrice with 200 ml chloroform
  5. washThe organic phase was washed successively with 500 ml water, 500 ml of 0.15 N HCl, 500 ml saturated aqueous NaHCO3
  6. dry with materialThe extract was dried over Na2SO4
  7. customthe solvent was removed under reduced pressure
  8. dissolutionThe obtained yellow residue was dissolved in 500 ml
  9. temperaturewarm hexane
  10. custom(5±3° C.) overnight
  11. customDuring this time, precipitation
  12. filtrationAfter filtration of the precipitate
  13. customthe solvent from the filtrate was removed under reduced pressure

Sources & evidence

ORD record
ord-4a8e4ce0b9084473b566026e33886c50
Source dataset
uspto-grants-2015_12
Patent number
US09206206B2

Reaction notes

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