Acetic Anhydride → Idramantone

HRID 2220027Notes

Reaction equation

HRID 2220027 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[CH:8]12[CH2:17]C3[CH2:13][CH:14]([CH2:16][CH:10](C3)[C:9]1=[O:18])[CH2:15]2.[OH-].[Na+]>[O-2].[O-2].[O-2].[Cr+6].C(O)(=O)C>[OH:7][C:5]12[CH2:6][CH:10]3[CH2:16][CH:14]([CH2:15][CH:8]([C:9]3=[O:18])[CH2:17]1)[CH2:13]2

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 64151Adamantanone

Product 1

HCID 64184Idramantone

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
17.5 °C

Procedure

Into a single neck 500 mL round bottom flask equipped with a magnetic stirrer and water bath, 75 parts of acetic acid containing 5 parts acetic anhydride was added. Twenty five parts of chromium trioxide was added in portions in 40 minutes while the temperature was maintained at 15-20° C. with water bath. Five parts of Adamantan-2-one was added in portions over a period of 15 minutes. Stirring was continued for one hour. The viscous reaction mixture was poured into cold 250 mL of aqueous 20% sodium hydroxide solution. The aqueous layer was extracted with 3×250 mL of ethyl acetate and washed with 2×250 mL of water and dried over sodium sulfate. Solvent was evaporated under reduced pressure and chromatographed on silica gel column using 75% ethyl acetate/hexane. The desired fractions were collected and solvent was evaporated to give a solid, yield 2.6 parts, single spot on silica gel TLC plate. The structure was confirmed on the basis of 1H NMR. The reaction proceeded as follows:

Workup

  1. customInto a single neck 500 mL round bottom flask equipped with a magnetic stirrer and water bath
  2. extractionThe aqueous layer was extracted with 3×250 mL of ethyl acetate
  3. washwashed with 2×250 mL of water
  4. dry with materialdried over sodium sulfate
  5. customSolvent was evaporated under reduced pressure
  6. customchromatographed on silica gel column
  7. customThe desired fractions were collected
  8. customsolvent was evaporated
  9. customto give a solid
  10. customyield 2.6 parts, single spot on silica gel TLC plate

Sources & evidence

ORD record
ord-d095291493014d73b7b8629e65d0169e
Source dataset
uspto-grants-2008_08
Patent number
US07416898B2

Reaction notes

Loading…