3-Methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)isoxazole → 2,6,6-Trimethyl-1-[3-amino-but-2-enoyl]-cyclohex-1-ene

HRID 917933Notes

Reaction equation

HRID 917933 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([C:7]2[C:12]([CH3:14])([CH3:13])[CH2:11][CH2:10][CH2:9][C:8]=2[CH3:15])[O:4][N:3]=1.[H][H]>C(O)C.[Pt]=O>[CH3:15][C:8]1[CH2:9][CH2:10][CH2:11][C:12]([CH3:13])([CH3:14])[C:7]=1[C:5](=[O:4])[CH:6]=[C:2]([NH2:3])[CH3:1]

Participants

5

Reactant 2

HCID 30160553-Methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)isoxazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 681338652,6,6-Trimethyl-1-[3-amino-but-2-enoyl]-cyclohex-1-eneYield 100%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent2×

Procedure

30.75 g (0.15 mole) of 3-methyl-5-[2,6,6-trimethylcyclohex-1-en-1-yl]-isoxazole were dissolved in 50 ml of dry ethanol and the solution was added to 1.396 g of a mixture of 82.9 % of platinum oxide in 600 ml of ethanol, the said mixture having previously been subjected to a hydrogenation. The alcoholic solution was then subjected to a hydrogenation at ordinary temperature and pressure and, after absorption of one equivalent of hydrogen, was filtered through a Celite carrier. After having been concentrated under reduced pressure, the residual mixture was recrystallized from hexene containing traces of ethanol to yield 30.91 g (yield 100 %) of 2,6,6-trimethyl-1-[3-amino-but-2-enoyl]-cyclohex-1-ene which exists in two interconvertible crystalline structures: m.p. 124.5° - 125.0° and 135°-136°.

Workup

  1. filtrationwas filtered through a Celite carrier
  2. concentrationAfter having been concentrated under reduced pressure
  3. customthe residual mixture was recrystallized from hexene containing traces of ethanol

Sources & evidence

ORD record
ord-630703b238ea47138c2e3cdc5a421914
Source dataset
uspto-grants-1976_07
Patent number
US03968161

Reaction notes

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