Hydrochloric Acid → HCID 86714078, compound

HRID 576395Notes

Reaction equation

HRID 576395 reaction equation
[C:1]([O:4][C@H:5]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:28]=[C:27]([CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:26]([Cl:36])=[C:25]3[C:20]=2[CH2:21][CH2:22][CH2:23][O:24]3)[O:7][C@@H:6]1[CH2:37][O:38][C:39](=[O:41])[CH3:40])(=[O:3])[CH3:2].[Al+3].[Cl-].[Cl-].[Cl-].[C:46](Cl)(=[O:48])[CH3:47].Cl>C(Cl)Cl>[C:1]([O:4][C@H:5]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:28]=[C:27]([CH2:29][C:30]3[CH:35]=[CH:34][C:33]([C:46](=[O:48])[CH3:47])=[CH:32][CH:31]=3)[C:26]([Cl:36])=[C:25]3[C:20]=2[CH2:21][CH2:22][CH2:23][O:24]3)[O:7][C@@H:6]1[CH2:37][O:38][C:39](=[O:41])[CH3:40])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 71110550HCID 71110550, compound

Product 1

HCID 86714078HCID 86714078, compoundYield 100.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the acetate 176 (500 mg, 0.85 mmol) in CH2Cl2 (20 mL) were added AlCl3 (691 mg, 5.18 mmol) and acetyl chloride (0.37 mL, 5.18 mmol) at 0° C. The mixture was warmed up to rt slowly and left at rt for 3 hours. The mixture was cooled to 0° C. and added aq. 1N HCl solution to quench the reaction. The mixture was extracted with EtOAc (100 mL). The organic layer was washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography to provide the product 177 (540 mg, quantitative yield).

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. customto quench
  3. customthe reaction
  4. extractionThe mixture was extracted with EtOAc (100 mL)
  5. washThe organic layer was washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-6f999d781f2e4de595458945c65dd2cd
Source dataset
uspto-grants-2015_05
Patent number
US09034921B2

Reaction notes

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