Ethyl Acetate → HCID 71110697, compound

HRID 576380Notes

Reaction equation

HRID 576380 reaction equation
C(O[C@H]1[C@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@H:8]([C:19]2[CH:24]=[CH:23][C:22]([CH2:25]O)=[C:21]([CH:27]([C:29]3[CH:34]=[CH:33][C:32]([CH2:35][CH3:36])=[CH:31][CH:30]=3)[OH:28])[CH:20]=2)[O:7][C@@H]1COC(=O)C)(=O)C.[CH3:42][CH2:43][O:44][C:45]([CH3:47])=[O:46]>C1(C)C=CC=CC=1>[C:45]([O:44][C@H:43]1[C@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@H:8]([C:19]2[CH:20]=[C:21]3[C:22](=[CH:23][CH:24]=2)[CH2:25][O:28][CH:27]3[C:29]2[CH:30]=[CH:31][C:32]([CH2:35][CH3:36])=[CH:33][CH:34]=2)[O:7][C@@H:42]1[CH2:10][O:11][C:12](=[O:14])[CH3:13])(=[O:46])[CH3:47]

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 86714071HCID 86714071, compound

Product 1

HCID 71110697HCID 71110697, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

Step 5) To a solution of compound 150 (500 mg, 0.87 mmol) in toluene (10.0 mL) was added p-TsCl (183 mg, 0.96 mmol) and the reaction mixture was heated to 90° C. for 12 h. The resulting mixture was diluted with EtOAc and washed with brine. The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The crude was purified by silica gel column chromatography to provide (2R,3R,4R,5S,6S)-2-(Acetoxymethyl)-6-(3-(4-ethylphenyl)-1,3-dihydroisobenzofuran-5-yl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (151, 380 mg, 79%) as a yellow solid.

Workup

  1. washwashed with brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-000c616063dd40f2b71dbcd25fd25681
Source dataset
uspto-grants-2015_05
Patent number
US09034921B2

Reaction notes

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