Water → HCID 22616346, compound

HRID 842955Notes

Reaction equation

HRID 842955 reaction equation
C1O[C:4]2([CH2:9][CH2:8][C:7](O)([C:10]3[C:19]4[O:18][CH2:17][CH2:16][O:15][C:14]=4[C:13]([O:20][CH3:21])=[CH:12][CH:11]=3)[CH2:6][CH2:5]2)[O:3]C1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[CH3:21][O:20][C:13]1[C:14]2[O:15][CH2:16][CH2:17][O:18][C:19]=2[C:10]([C:7]2[CH2:8][CH2:9][C:4](=[O:3])[CH2:5][CH:6]=2)=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 521998p-Toluenesulfonic acid monohydrateHCID 12052213HCID 12052213, compound

Product 1

HCID 22616346HCID 22616346, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To the mixture of Compound 2a (1.2 g, 3.6 mmol) obtained in Step A of Example 2 and p-toluenesulfonic acid monohydrate (1.2 mg, 0.0063 mmol) were added water (70 mL) and toluene (140 mL ), followed by refluxing for 4 hours. The mixture was allowed to cool, the mixture was extracted with toluene, and the extract was washed with a saturated aqueous solution of sodium bicarbonate and then with brine. The mixture was dried over sodium sulfate, the solvent was evaporated, and the residue was purified by silica gel column chromatography (eluted with hexane/ethyl acetate=2/1) to give Compound 16 (0.88 g, 94%) as a pale yellow solid.

Workup

  1. temperatureby refluxing for 4 hours
  2. temperatureto cool
  3. extractionthe mixture was extracted with toluene
  4. washthe extract was washed with a saturated aqueous solution of sodium bicarbonate
  5. dry with materialThe mixture was dried over sodium sulfate
  6. customthe solvent was evaporated
  7. customthe residue was purified by silica gel column chromatography (eluted with hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-e676341a128347c5a73d940c927872c2
Source dataset
uspto-grants-2002_04
Patent number
US06376535B2

Reaction notes

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