Diethyl Ether → 3-O-Octadecyl-2-O-tosyl-1-O-tritylglycerol

HRID 1741140Notes

Reaction equation

HRID 1741140 reaction equation
[CH2:1]([O:19][CH2:20][CH:21]([CH2:23][O:24][C:25]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[OH:22])[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][CH2:16][CH2:17][CH3:18].[C:44]1([CH3:54])[CH:49]=[CH:48][C:47]([S:50](Cl)(=[O:52])=[O:51])=[CH:46][CH:45]=1.C(OCC)C>O>[CH2:1]([O:19][CH2:20][CH:21]([CH2:23][O:24][C:25]([C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1)([C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[O:22][S:50]([C:47]1[CH:48]=[CH:49][C:44]([CH3:54])=[CH:45][CH:46]=1)(=[O:52])=[O:51])[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][CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 73974-Toluenesulfonyl chlorideHCID 128968481-(Octadecyloxy)-3-(triphenylmethoxy)propan-2-ol

Product 1

HCID 135065293-O-Octadecyl-2-O-tosyl-1-O-tritylglycerol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
4 °C

Procedure

A solution of 1-O-octadecyl-3-O-trityl-glycerol (173.51 g, 295.63 mmol) in 895 mL water-free pyridine is added dropwise to a solution of p-toluenesulfonyl chloride (88.49 g, 464.15 mmol) in 670 mL water-free pyridine with constant stirring. The reaction mixture is kept at ambient temperature (20-23° C.) for two days. Diethyl ether (2.8 L) is added, and the organic phase is washed six times with water, twice with 0.5 N HCl (500 mL each), twice with diluted aqueous sodium carbonate, and then washed with water until neutral. After drying the organic phase over sodium sulfate, the solvent is removed under vacuum. The residue is triturated with isopropanol (1140 mL) with stirring until the product crystallizes. After cooling to 4° C., the product, 1-O-octadecyl-2-O-p-toluenesulfonyl-3-O-trityl-glycerol, is isolated by filtration, washed with isopropanol and dried under vacuum. Yield: 190.14 g (86.91%); m.p. 56-58° C.; Rf value (TLC on silica gel 60) of 0.38 with benzene as the developing solvent; and Rf value of 0.74 with benzene/methanol (50/2).

Workup

  1. customis kept at ambient temperature
  2. custom(20-23° C.)
  3. customfor two days
  4. washthe organic phase is washed six times with water
  5. washtwice with 0.5 N HCl (500 mL each), twice with diluted aqueous sodium carbonate, and then washed with water until neutral
  6. dry with materialAfter drying the organic phase over sodium sulfate
  7. customthe solvent is removed under vacuum
  8. customThe residue is triturated with isopropanol (1140 mL)
  9. customcrystallizes

Sources & evidence

ORD record
ord-d285e678c59640e2a5000813425ffbce
Source dataset
uspto-grants-1999_10
Patent number
US05972982

Reaction notes

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