Calcium Carbonate → 17alpha-Ethyl-3-methoxyestra-1,3,5(10),8-tetraen-17-ol

HRID 1077239Notes

Reaction equation

HRID 1077239 reaction equation
[C:1]([C@:3]1([OH:23])[CH2:8][CH2:7][C@H:6]2[C:9]3[CH2:10][CH2:11][C:12]4[CH:13]=[C:14]([O:21][CH3:22])[CH:15]=[CH:16][C:17]=4[C:18]=3[CH2:19][CH2:20][C@:4]12[CH3:5])#[CH:2].C(=O)([O-])[O-].[Ca+2].[H][H]>C1C=CC=CC=1>[CH2:1]([C@:3]1([OH:23])[CH2:8][CH2:7][C@H:6]2[C:9]3[CH2:10][CH2:11][C:12]4[CH:13]=[C:14]([O:21][CH3:22])[CH:15]=[CH:16][C:17]=4[C:18]=3[CH2:19][CH2:20][C@:4]12[CH3:5])[CH3:2]

Participants

5

Reactant 3

HCID 10112Calcium CarbonateHCID 8673349117alpha-Ethynyl-3-methoxyestra-1,3,5(10),8-tetraen-17-olHCID 178418361HCID 178418361, compound2×

Product 1

HCID 6814549517alpha-Ethyl-3-methoxyestra-1,3,5(10),8-tetraen-17-olYield 63.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

Add dl-17α-ethynyl-3-methoxyestra-1,3,5(10),8-tetraen-17-ol (7 g) in benzene (75 ml) to a suspension of prehydrogenated 2% palladised calcium carbonate (3 g) in benzene (50 ml), and shake in an atmosphere of hydrogen until two molecular equivalents of hydrogen (1.030 ml) have been absorbed. Filter the catalyst, evaporate the solvent and recrystallize the residue twice from methanol to obtain dl-17α-ethyl-3-methoxyestra-1,3,5(10),8-tetraen-17-ol (4.5 g), m.p. 105°-120°; ultraviolet absorption maximum 278 mμ (ε12,000); infrared absorption peaks at 295 μ, 6.25 μ.

Workup

  1. customhave been absorbed
  2. filtrationFilter the catalyst
  3. customevaporate the solvent
  4. customrecrystallize the residue twice from methanol

Sources & evidence

ORD record
ord-a99069b1a6194a67bef9f207bf8c694a
Source dataset
uspto-grants-1976_05
Patent number
US03959322

Reaction notes

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