Oxygen → Idramantone

HRID 1019285Notes

Reaction equation

HRID 1019285 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.C([OH:26])(C1C=CC=CC=1)C1C=CC=CC=1.ON1C(=O)C2=CC=CC=C2C1=O.O=O>C([O-])(=O)C.[Co+2].C([O-])(=O)C.C(#N)C1C=CC=CC=1>[OH:1][C:2]12[CH2:3][CH:4]3[CH2:10][CH:8]([CH2:7][CH:6]([O:26][C:5]3=[O:12])[CH2:11]1)[CH2:9]2.[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

Participants

8

Reactant 4

HCID 977OxygenHCID 7037BenzhydrolHCID 10665N-HydroxyphthalimideHCID 64184Idramantone

Product 2

HCID 64184IdramantoneHCID 3239817HCID 3239817, compound

Reagents, catalysts & solvents 2

HCID 6277Cobalt diacetateCatalystHCID 7505BenzonitrileSolvent

Procedure

A mixture of 100 mmol of 5-hydroxy-2-adamantanone, 200 mmol of benzhydrol, 10 mmol of N-hydroxyphthalimide, 0.1 mmol of cobalt(II) acetate, and 200 ml of benzonitrile was stirred at 75° C. in an oxygen atmosphere (1 atm) for 6 hours. A reaction mixture was concentrated and was then subjected to column chromatography on a silica gel to yield 1-hydroxy-4-oxatricyclo[4.3.1.13,8]undecan-5-one of the following formula in a yield of 48% with a conversion rate from 5-hydroxy-2-adamantanone of 67%.

Workup

  1. concentrationA reaction mixture was concentrated

Sources & evidence

ORD record
ord-c93d060989424ad1bc1f039383e94906
Source dataset
uspto-grants-2002_11
Patent number
US06486330B1

Reaction notes

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