Methane → HCID 54231473, compound

HRID 1077160Notes

Reaction equation

HRID 1077160 reaction equation
[CH2:1]([C@:3]12[CH2:11][CH2:10][C:9]3[C:12]4[CH:13]=[CH:14][C:15]([O:20][C:21](=[O:23])[CH3:22])=[CH:16][C:17]=4[CH2:18][CH2:19][C:8]=3[C:7]1=[CH:6][CH2:5][C:4]2=[O:24])[CH3:2].C>C1C=CC=CC=1>[CH2:1]([C@:3]12[CH2:11][CH2:10][C:9]3[C:12]4[CH:13]=[CH:14][C:15]([O:20][C:21](=[O:23])[CH3:22])=[CH:16][C:17]=4[CH2:18][CH2:19][C:8]=3[C@@H:7]1[CH2:6][CH2:5][C:4]2=[O:24])[CH3:2]

Participants

4

Reactant 2

HCID 297MethaneHCID 54283311HCID 54283311, compound

Product 1

HCID 54231473HCID 54231473, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Hydrogenate 13β-ethyl-3-acetoxygona-1,3,5(10),8,14-pentaen-17-one (1.8 g.) dissolved in benzene (25 ml.) at atmospheric pressure in the presence of 10% palladized charcoal (100 mg.). After 1.1 molar equivalents of hydrogen has been absorbed (ca. 12 hr.) filter off the catalyst, evaporate the filtrate under reduced pressure and recrystallize the residue from ethanol. Filter the red product through `Florisil` (60 g.) with benzene-petroleum (3:1), remove the solvent and recrystallize the product from ethanol to obtain the title product, m.p. 132.5°-134.5°; ultra-violet absorption peak at 277 mμ (ε 12,800).

Workup

  1. customAfter 1.1 molar equivalents of hydrogen has been absorbed (ca. 12 hr.)
  2. filtrationfilter off the catalyst
  3. customevaporate the filtrate under reduced pressure
  4. customrecrystallize the residue from ethanol
  5. filtrationFilter the red product through `Florisil` (60 g.) with benzene-petroleum (3:1)
  6. customremove the solvent
  7. customrecrystallize the product from ethanol

Sources & evidence

ORD record
ord-ab499d468fc74993ba4a2c5e56b2f70b
Source dataset
uspto-grants-1976_05
Patent number
US03959322

Reaction notes

Loading…