Acetic Anhydride → HCID 2843184, compound

HRID 386511Notes

Reaction equation

HRID 386511 reaction equation
[OH:1][C:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([C:5]3=[O:12])[CH2:3]1)[CH2:9]2.CN(C1C=CC=CN=1)C.[C:22](OC(=O)C)(=[O:24])[CH3:23]>ClCCl>[O:12]=[C:5]1[CH:6]2[CH2:7][CH:8]3[CH2:9][C:2]([O:1][C:22](=[O:24])[CH3:23])([CH2:3][CH:4]1[CH2:10]3)[CH2:11]2

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 218852-DimethylaminopyridineHCID 64184Idramantone

Product 1

HCID 2843184HCID 2843184, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 5-hydroxy-2-adamantanone (2.6 g, 15.66 mmoles) in dichloromethane (DCM) (50 mL) was treated with dimethylaminopyridine (DMAP) (2.1 g, 17 mmoles) and acetic anhydride (2.3 mL, 23 mmoles) and stirred overnight at 50° C. The solvent was removed under reduced pressure and the residue was partitioned between water and ethyl acetate. The aqueous layer was extracted twice with ethyl acetate. Combined organic extracts were washed with water, dried (MgSO4) and filtered. The filtrate was concentrated under reduced pressure to provide the title compound as an off-white solid.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was partitioned between water and ethyl acetate
  3. extractionThe aqueous layer was extracted twice with ethyl acetate
  4. washCombined organic extracts were washed with water
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b063b26f268341d99b98df2d08e4fb65
Source dataset
uspto-grants-2013_02
Patent number
US08372841B2

Reaction notes

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