Acetic Acid → HCID 70459693, compound

HRID 1111058Notes

Reaction equation

HRID 1111058 reaction equation
C(O)(=O)C.Cl[CH2:6][C:7](=[O:30])[C@@:8]1([OH:29])[C@:25]2([CH3:26])[C@H:11]([C@H:12]3[C@H:22]([CH2:23][CH2:24]2)[C@:20]2([CH3:21])[C:15](=[CH:16][C:17](=[O:27])[CH2:18][CH2:19]2)[CH2:14][CH2:13]3)[CH2:10][C:9]1=[CH2:28]>C(OCC)(=O)C.[Zn]>[OH:29][C@@:8]1([C@:25]2([CH3:26])[C@H:11]([C@H:12]3[C@H:22]([CH2:23][CH2:24]2)[C@:20]2([CH3:21])[C:15](=[CH:16][C:17](=[O:27])[CH2:18][CH2:19]2)[CH2:14][CH2:13]3)[CH2:10][C:9]1=[CH2:28])[C:7](=[O:30])[CH3:6]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 86743894HCID 86743894, compound

Product 1

HCID 70459693HCID 70459693, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Zinc dust (0.030 mg) and glacial acetic acid (0.13 ml) is added to a solution of 21-chloro-17β-hydroxy-16-methylenepregn-4-ene-3,20-dione (III, EXAMPLE 40B, 0.050 g) in ethyl acetate (1.5 ml). The reaction system is purged with nitrogen and warmed to 45°. After stirring for 16.5 hr, THF (5 ml) is added and the mixture is filtered thru celite to remove the remaining zinc. The filtrate is then partitioned between water (5 ml) and ether (5 ml). The organic extract is washed with sodium bicarbonate (5%) and water, dried over sodium sulfate and concentrated to give the title compound, NMR (CD2Cl2) 0.87, 1.17, 2.20, 3.40, 5.10 and 5.65 δ.

Workup

  1. customThe reaction system is purged with nitrogen
  2. temperaturewarmed to 45°
  3. additionTHF (5 ml) is added
  4. filtrationthe mixture is filtered thru celite
  5. customto remove the remaining zinc
  6. customThe filtrate is then partitioned between water (5 ml) and ether (5 ml)
  7. extractionThe organic extract
  8. washis washed with sodium bicarbonate (5%) and water
  9. dry with materialdried over sodium sulfate
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-3979252f7565490f80e6c0c80a891b13
Source dataset
uspto-grants-1990_12
Patent number
US04977255

Reaction notes

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