Butanedione → HCID 178465752, compound

HRID 1369190Notes

Reaction equation

HRID 1369190 reaction equation
[CH2:1]1[C@@H:10]2[C@@H:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:4][CH2:3][CH2:2]1.[C:11](C(C)=O)([CH3:13])=[O:12].ON1[C:22](=[O:23])[C:21]2=CC=CC=C2C1=O.O=O>C([O-])(=O)C.[Co+2].C([O-])(=O)C.C(O)(=O)C>[C:11]([C@@:5]12[CH2:6][CH2:7][CH2:8][CH2:9][C@@H:10]1[CH2:1][CH2:2][CH2:3][CH2:4]2)(=[O:12])[CH3:13].[C:22]([C@@:5]12[CH2:6][CH2:7][CH2:8][CH2:9][C@:10]1([OH:12])[CH2:1][CH2:2][CH2:3][CH2:4]2)(=[O:23])[CH3:21]

Participants

8

Reactant 4

HCID 650ButanedioneHCID 977OxygenHCID 10665N-HydroxyphthalimideHCID 178420443HCID 178420443, compound

Product 2

HCID 178465752HCID 178465752, compoundHCID 178465753HCID 178465753, compound

Reagents, catalysts & solvents 2

HCID 6277Cobalt diacetateCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 0.3 mol of cis-decalin, 1.8 mol of biacetyl, 30 mmol of N-hydroxyphthalimide, 1.5 mmol of cobalt(II) acetate, and 300 ml of acetic acid was stirred at 60° C. in an oxygen atmosphere at atmospheric pressure for 4 hours. The reaction mixture was concentrated to about 20% by weight, and was extracted with ethyl acetate, and the extract was concentrated and was then subjected to column chromatography on a silica gel to yield 4a-acetyl-cis-decalin and 4a-acetyl-8a-hydroxy-cis-decalin.

Workup

  1. concentrationThe reaction mixture was concentrated to about 20% by weight
  2. extractionwas extracted with ethyl acetate
  3. concentrationthe extract was concentrated

Sources & evidence

ORD record
ord-80f24cb87b9643598bd8975af6e1ba4e
Source dataset
uspto-grants-2003_06
Patent number
US06576787B1

Reaction notes

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