Acetic Anhydride → HCID 22258086, compound

HRID 1611001Notes

Reaction equation

HRID 1611001 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][O:9][C:10]1[C:15]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[Cl:24])=[CH:14][CH:13]=[CH:12][C:11]=1[CH:25]([OH:29])[C:26]([OH:28])=[O:27].C(OC(=O)C)(=O)C>CS(C)=O.O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][O:9][C:10]1[C:15]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[Cl:24])=[CH:14][CH:13]=[CH:12][C:11]=1[C:25](=[O:29])[C:26]([OH:28])=[O:27]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 9932554HCID 9932554, compound

Product 1

HCID 22258086HCID 22258086, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a stirred solution of Example 1 Part B compound (400 mg, 0.867 mmol) in DMSO (1 mL) at 90° C. was added acetic anhydride (0.1 mL, 1 mmol) over 1 h. After an additional 3 h, the reaction mixture was cooled, diluted with water and extracted three times with ether. The organic extracts were combined, washed with brine, dried (Na2SO4) and evaporated. Purification by flash chromatography on silica gel provided the title compound, 382 mg (96% yield). LC/MS gave the correct molecular ion [(M+Na)+=481] for the desired compound.

Workup

  1. temperaturethe reaction mixture was cooled
  2. extractionextracted three times with ether
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customPurification by flash chromatography on silica gel

Sources & evidence

ORD record
ord-a27f706f025a4575951f27d7a10827c8
Source dataset
uspto-grants-2006_01
Patent number
US06984645B2

Reaction notes

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