Trityl chloride → HCID 131734283, compound

HRID 1501910Notes

Reaction equation

HRID 1501910 reaction equation
[CH3:1][CH:2]([CH:9]([CH:21]([CH:23]([CH2:25][OH:26])[OH:24])[OH:22])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[C:27]1([C:33]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)Cl)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(N(CC)CC)C>C1COCC1.C(#N)C>[CH3:1][CH:2]([CH:9]([C@@H:21]([CH:23]([CH2:25][O:26][C:33]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1)[C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)[OH:24])[OH:22])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

6

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 87357320HCID 87357320, compound

Product 1

HCID 131734283HCID 131734283, compoundYield 92.7%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

17 grams of 1-(2-octyl)dodecyl-glycerol (dried by azeotropic distillation with benzene) was dissolved in a mixture of dry THF (400 ml) and dry acetonitrile (160 ml). Triphenylchloromethane (15.8 grams) and dry triethylamine (14 ml) were added, and the reaction mixture was refluxed for 17 hours. The reaction mixture was cooled to room temperature, poured on ice (1 kilogram), transferred to a separatory funnel and extracted with diethyl ether (3×200 ml). The combined organic phase was washed consecutively with water (200 ml), dilute (1.5%) sulfuric acid (2×100 ml), water (200 ml), concentrated aqueous sodium bicarbonate (200 ml) and again with water (200 ml). The organic phase was dried over anhydrous sodium sulfate, the solvent was removed under reduced pressure, and the obtained crude product was purified by chromatography on a silica gel (350 grams) column. 26 grams of pure (S)-1-(2-octyl)dodecyl-3-trityl-glycerol was eluted by hexane followed by a mixtures of hexane and chloroform (50-100%) as a yellow oil. The yield was 92.7%.

Workup

  1. temperaturethe reaction mixture was refluxed for 17 hours
  2. additionpoured on ice (1 kilogram)
  3. customtransferred to a separatory funnel
  4. extractionextracted with diethyl ether (3×200 ml)
  5. washThe combined organic phase was washed consecutively with water (200 ml)
  6. additiondilute (1.5%) sulfuric acid (2×100 ml), water (200 ml), concentrated aqueous sodium bicarbonate (200 ml)
  7. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  8. customthe solvent was removed under reduced pressure
  9. customthe obtained crude product
  10. customwas purified by chromatography on a silica gel (350 grams) column
  11. wash26 grams of pure (S)-1-(2-octyl)dodecyl-3-trityl-glycerol was eluted by hexane

Sources & evidence

ORD record
ord-2fa3f6edf74c461c8e582ae66471999a
Source dataset
uspto-grants-2015_12
Patent number
US09206206B2

Reaction notes

Loading…