13beta-Methyl-3-hydroxygona-1,3,5(10),8,14-pentaen-17one → 8,9-Dehydroestrone

HRID 1414975Notes

Reaction equation

HRID 1414975 reaction equation
[CH3:1][C@:2]12[CH2:10][CH2:9][C:8]3[C:11]4[CH:12]=[CH:13][C:14]([OH:19])=[CH:15][C:16]=4[CH2:17][CH2:18][C:7]=3[C:6]1=[CH:5][CH2:4][C:3]2=[O:20]>C1C=CC=CC=1.[H][H].C>[CH3:1][C@:2]12[CH2:10][CH2:9][C:8]3[C:11]4[CH:12]=[CH:13][C:14]([OH:19])=[CH:15][C:16]=4[CH2:17][CH2:18][C:7]=3[C@@H:6]1[CH2:5][CH2:4][C:3]2=[O:20]

Participants

5

Reactant 1

HCID 2723425813beta-Methyl-3-hydroxygona-1,3,5(10),8,14-pentaen-17one

Product 1

HCID 64514728,9-DehydroestroneYield 69.5%

Reagents, catalysts & solvents 3

HCID 297MethaneCatalystHCID 241BenzeneSolventHCID 178418361HCID 178418361, compoundSolvent2×

Procedure

Shake 13β-methyl-3-hydroxygona-1,3,5(10), 8,14-pentaen-17-one (0.05 g) in benzene (25 cc) in hydrogen at atmospheric pressure using a 10% palladized charcoal catalyst (0.025 g). Hydrogenation becomes very slow when 1.1 moles hydrogen has been absorbed. Filter and evaporate to obtain the title product (0.035 g), recrystallize from methanol to get pale blue crystals, m.p. 225°-228°, melting to a red liquid; ultraviolet absorption peak at 280 mμ (ε12,000).

Workup

  1. customhas been absorbed
  2. filtrationFilter
  3. customevaporate

Sources & evidence

ORD record
ord-6229783cdf7d476689f9053adb8206dc
Source dataset
uspto-grants-1977_01
Patent number
US04002746

Reaction notes

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