Methanol → HCID 86618686, compound

HRID 1436997Notes

Reaction equation

HRID 1436997 reaction equation
S(=O)(=O)(O)O.[CH3:6][C:7]1[CH2:8][CH2:9][CH:10]=[C:11]([C:22]([OH:24])=[O:23])[CH2:12][CH2:13][C@@H:14]2[C:18](=[CH2:19])[C:17](=[O:20])[O:16][C@@H:15]2[CH:21]=1.[CH3:25]O>[Cl-].[Na+].O>[CH3:6][C:7]1[CH2:8][CH2:9][CH:10]=[C:11]([C:22]([O:24][CH3:25])=[O:23])[CH2:12][CH2:13][C@@H:14]2[C:18](=[CH2:19])[C:17](=[O:20])[O:16][C@@H:15]2[CH:21]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 68906616HCID 68906616, compound

Product 1

HCID 86618686HCID 86618686, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

Concentrated sulfuric acid (2 mL) was added slowly to a solution of the acid product of Example 1 (0.1 mmol) in 20 mL absolute methanol. The mixture was refluxed overnight, cooled to room temperature, and diluted with brine. The resultant solution was extracted with 3×20 mL CHCl3. The combined organic layers were washed with a saturated sodium bicarbonate solution and brine, dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by column chromatography to provide the desired product in a yield of 82%.

Workup

  1. temperatureThe mixture was refluxed overnight
  2. extractionThe resultant solution was extracted with 3×20 mL CHCl3
  3. washThe combined organic layers were washed with a saturated sodium bicarbonate solution and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-643659956fb0484096422db0b8d5b841
Source dataset
uspto-grants-2009_11
Patent number
US07622465B2

Reaction notes

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