HCID 86601497, compound → HCID 11037390, compound

HRID 1295973Notes

Reaction equation

HRID 1295973 reaction equation
CC1C=CC(S(O[C@@H:12]2[C@H:16]([O:17][S:18]([C:21]3[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=3)(=[O:20])=[O:19])OC(C)(C)[O:13]2)(=O)=O)=CC=1>O1CCCC1>[CH3:27][C:24]1[CH:23]=[CH:22][C:21]([S:18]([O:17][CH2:16][C@@H:12]([OH:13])[C@H:12]([OH:13])[CH2:16][O:17][S:18]([C:21]2[CH:22]=[CH:23][C:24]([CH3:27])=[CH:25][CH:26]=2)(=[O:19])=[O:20])(=[O:19])=[O:20])=[CH:26][CH:25]=1

Participants

3

Reactant 1

HCID 86601497HCID 86601497, compound

Product 1

HCID 11037390HCID 11037390, compoundYield 221.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A solution of (4R,5S)-2,2-dimethyl-5-[(4-methylphenyl)sulfonyl]oxy-1,3-dioxolan-4-yl 4-methyl-1-benzenesulfonate (5.07 g, 10.8 mmol) in a tetrahydrofuran (50 ml) −10% perchloric acid water (50 ml) mixed solvent was stirred at 50° C. for 7 hours. The tetrahydrofuran was distilled off under reduced pressure, extraction was performed with ethyl acetate and the extract was washed with brine. After drying with anhydrous magnesium sulfate, the solvent was distilled off to yield a crude product which was then purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (5.14 g). This was used without further purification for the following reaction.

Workup

  1. distillationThe tetrahydrofuran was distilled off under reduced pressure, extraction
  2. washthe extract was washed with brine
  3. dry with materialAfter drying with anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off
  5. customto yield a crude product which
  6. customwas then purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-7116f49065ce4b53ae416d9aaf147b97
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

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