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

HRID 1415059Notes

Reaction equation

HRID 1415059 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 2.95 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-980b61bcfc8a4430b2a328930d104902
Source dataset
uspto-grants-1977_01
Patent number
US04002746

Reaction notes

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