Methanol → HCID 19835441, compound

HRID 478107Notes

Reaction equation

HRID 478107 reaction equation
[CH:1]#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH:14]([O:17][CH2:18][CH:19]([CH2:21][O:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][O:28]CCOC(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[OH:20])[CH2:15][CH3:16].[H-].[Na+].[CH3:53]I.CO>C1COCC1>[CH:1]#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH:14]([O:17][CH2:18][CH:19]([CH2:21][O:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][OH:28])[O:20][CH3:53])[CH2:15][CH3:16]

Participants

6

Reactant 4

HCID 887MethanolHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 19835447HCID 19835447, compound

Product 1

HCID 19835441HCID 19835441, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Then 1.8 g (6.12 millimole) of this epoxy derivative was converted into crude 1-O-(hexadecyn-14-yl)-3-O-[2-(2-trityloxyethoxyethoxy)ethyl]glycerol by following the procedure described in Working Example 62. The crude product was dissolved in 20 ml of THF, to which 367 mg (9.18 millimole) of 60% sodium hydride was added, and the mixture was stirred at room temperature for 1 hour. To the reaction mixture was added dropwise 1.74 g (12.2 millimole) of methyl iodide in 4 ml of THF over a period of 20 minutes. The reaction mixture was stirred at room temperature overnight, to which was added 1 ml of methanol, and the mixture was concentrated under reduced pressure. The residue was extracted with hexane, and the hexane layer was washed with water, and then hexane was distilled off. To the residue were added 45 ml of dioxane, 30 ml of methanol and 12 ml of 2N hydrochloric acid, and the mixture was stirred at 70° C. for 1 hour. The reaction mixture was cooled, neutralized with saturated aqueous solution of sodium hydrogencarbonate, and concentrated under reduced pressure, and then the residue was extracted with ethyl acetate. The organic layer was washed with water and dried, and the solvent was distilled off. The residue was subjected to silica gel (50 g) column chromatography, and eluted with chloroform-methanol (9:1), to give the above-captioned compound as colorless oil.

Workup

  1. additionwas added
  2. stirringThe reaction mixture was stirred at room temperature overnight, to which
  3. concentrationthe mixture was concentrated under reduced pressure
  4. extractionThe residue was extracted with hexane
  5. washthe hexane layer was washed with water
  6. distillationhexane was distilled off
  7. additionTo the residue were added 45 ml of dioxane, 30 ml of methanol and 12 ml of 2N hydrochloric acid
  8. stirringthe mixture was stirred at 70° C. for 1 hour
  9. temperatureThe reaction mixture was cooled
  10. concentrationconcentrated under reduced pressure
  11. extractionthe residue was extracted with ethyl acetate
  12. washThe organic layer was washed with water
  13. customdried
  14. distillationthe solvent was distilled off
  15. washeluted with chloroform-methanol (9:1)

Sources & evidence

ORD record
ord-73686c39ce55479f9d0c0b539c74daeb
Source dataset
uspto-grants-1989_12
Patent number
US04889953

Reaction notes

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