HCID 23460857, compound → HCID 53786818, compound

HRID 65577Notes

Reaction equation

HRID 65577 reaction equation
[CH3:1][C:2]1([CH3:29])[CH:11]([N:12]([CH3:23])[S:13]([C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=2)(=[O:15])=[O:14])[CH2:10][C:9]2[C:4](=[CH:5][C:6]([O:24][CH3:25])=[CH:7][CH:8]=2)[C:3]1([C:27]#[CH:28])[OH:26]>[Pd].C(OCC)(=O)C>[CH3:1][C:2]1([CH3:29])[CH:11]([N:12]([CH3:23])[S:13]([C:16]2[CH:17]=[CH:18][C:19]([CH3:22])=[CH:20][CH:21]=2)(=[O:15])=[O:14])[CH2:10][C:9]2[C:4](=[CH:5][C:6]([O:24][CH3:25])=[CH:7][CH:8]=2)[C:3]1([CH:27]=[CH2:28])[OH:26]

Participants

4

Reactant 1

HCID 23460857HCID 23460857, compound

Product 1

HCID 53786818HCID 53786818, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 205 g of 2,2-dimethyl-1-ethinyl-7-methoxy-3-(N-methyl-p-toluenesulphonamido)-1,2,3,4-tetrahydro-1-naphthol, 0.8 g of 0,5% palladium on calcium carbonate, 0.8 g 5% palladium on charcoal and 1000 ml of ethyl acetate is submitted to hydrogenation at atmospheric pressure and room temperature. After the absorption of 1200 ml of hydrogen the catalysts are removed by filtration. The solution is concentrated by evaporation in vacuo of most of the solvent, whereafter the product crystallizes as white crystals melting at 152°-154° C. Yield 95%.

Workup

  1. customis submitted to hydrogenation at atmospheric pressure and room temperature
  2. customAfter the absorption of 1200 ml of hydrogen the catalysts
  3. customare removed by filtration
  4. concentrationThe solution is concentrated by evaporation in vacuo of most of the solvent
  5. customwhereafter the product crystallizes as white crystals melting at 152°-154° C

Sources & evidence

ORD record
ord-901d954f193c43aca74ff7cd531634b3
Source dataset
uspto-grants-1978_12
Patent number
US04128548

Reaction notes

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