HCID 14482100, compound → HCID 10698078, compound

HRID 974684Notes

Reaction equation

HRID 974684 reaction equation
[CH2:1]([O:17][CH2:18][C@H:19]([CH2:26][O:27][C:28]([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[O:20]C1C=CON=1)[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].[H][H]>O1CCCC1.C(O)C.[Pd]>[CH2:1]([O:17][CH2:18][C@H:19]([CH2:26][O:27][C:28]([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)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=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 2

HCID 14482100HCID 14482100, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 10698078HCID 10698078, compoundYield 84.7%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

4.400 g of 1-O-hexadecyl-2-O-(3-isoxazolyl)-3-O-triphenylmethyl-sn-glycerol described in Preparation 4 was dissolved in a mixture of 10 ml of tetrahydrofuran and 90 ml of ethanol and the solution was placed in a Paar apparatus and then shaken in the presence of 4.40 g of 10% w/w palladium-on-carbon in an atmosphere of hydrogen at 4 times atmospheric pressure for 49 hours. After removing the catalyst by filtration, 0.635 g of potassium carbonate was added to the reaction mixture, and the mixture was stirred at room temperature for 30 minutes. After filtering off the insoluble material, the solvent was distilled off and the residue was subjected to column chromatography through 100 g of silica gel. 3.327 g of 1-O-hexadecyl-3-O-triphenylmethyl-sn-glycerol was obtained from the fractions eluted with mixtures of hexane and diethyl ether ranging from 19:1 to 9:1 by volume, as white crystals melting at 49°-50° C.

Workup

  1. customAfter removing the catalyst
  2. filtrationby filtration, 0.635 g of potassium carbonate
  3. additionwas added to the reaction mixture
  4. filtrationAfter filtering off the insoluble material
  5. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-48346fd1135d4837a45524c7fab244f0
Source dataset
uspto-grants-1991_11
Patent number
US05068340

Reaction notes

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