Water → HCID 67327525, compound

HRID 1501901Notes

Reaction equation

HRID 1501901 reaction equation
[CH2:1]([O:17][CH2:18][C@H:19]([CH2:21][O:22][C:23]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=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].[OH-].[K+].O>C1C=CC=CC=1>[CH2:1]([O:17][CH2:18][C@H:19]([CH2:21][O:22][C:23]([C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[O:20][CH2:1][CH2:2][CH:3]=[CH:4][CH2:5][CH3:6])[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

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 10698078HCID 10698078, compound

Product 1

HCID 67327525HCID 67327525, compoundYield 195.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

10.60 grams of (R)-1-hexadecyl-3-trityl-sn-glycerol was dissolved in a mixture of 50 ml benzene and 50 ml petroleum ether. 16.65 grams of powdered KOH was added, and the reaction mixture was heated to reflux under nitrogen. A solution of 10 ml 3-hexenyl-1-methane sulfonate in 50 ml benzene and 200 ml petroleum ether was added dropwise to the refluxing reaction mixture over the course of over 10 hours while removing the water formed in the reaction by azeotropic distillation. After completion of the addition, stirring was continued for 2 hours. The reaction mixture was cooled to room temperature and 200 ml water was added. The mixture was extracted thrice with 200 ml diethyl ether, the combined organic phase was washed thrice with 200 ml water, and the solvent was removed under reduced pressure, yielding 11.88 grams of crude (R)-1-hexadecyl-2-(3 hexenyl)-3-trityl-sn-glycerol. The 1-hexadecyl-2-(3-hexenyl)-3-trityl-glycerol was dissolved in 100 ml methanol, 4 ml concentrated HCl was added, and the resulting solution was refluxed for 4 hours. 100 ml water was added and the mixture extracted four times with 100 ml diethyl ether. The combined organic phase was washed with 100 ml water and dried over anhydrous Na2SO4, and the solvent was removed under reduced pressure. The obtained residue was dissolved in hexane and stored at 4° C. overnight. Filtration of the precipitate and removal of the solvent under reduced pressure yielded 10.08 grams of crude product. This product was purified by chromatography on silica gel (95.91 grams). 3.71 grams of the product, (S)-1-hexadecyl-2-(3′-hexenyl)-sn-glycerol, was eluted with a 1:1 (v/v) mixture of hexane and chloroform, followed by chloroform and then chloroform with 2% acetone.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux under nitrogen
  3. customwhile removing the water
  4. customformed in the reaction by azeotropic distillation
  5. additionAfter completion of the addition
  6. extractionThe mixture was extracted thrice with 200 ml diethyl ether
  7. washthe combined organic phase was washed thrice with 200 ml water
  8. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-8c977c68bdb54c8fbc66aa823d703ae3
Source dataset
uspto-grants-2015_12
Patent number
US09206206B2

Reaction notes

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