HCID 22789124, compound → HCID 22789125, compound

HRID 1606289Notes

Reaction equation

HRID 1606289 reaction equation
[CH3:1][O:2][C:3]1[C:20]2[C:19]3[CH2:18][CH2:17][C@@:15]4([CH3:16])[C:11](=[CH:12][CH2:13][C@@H:14]4[O:21][C:22](=[O:24])[CH3:23])[C:10]=3[CH2:9][CH2:8][C:7]=2[CH:6]=[C:5]([O:25][CH3:26])[CH:4]=1>[Pd].C([O-])([O-])=O.[Ca+2].C1COCC1>[CH3:1][O:2][C:3]1[C:20]2[C:19]3[CH2:18][CH2:17][C@@:15]4([CH3:16])[C@@H:11]([CH2:12][CH2:13][C@@H:14]4[O:21][C:22](=[O:24])[CH3:23])[C:10]=3[CH2:9][CH2:8][C:7]=2[CH:6]=[C:5]([O:25][CH3:26])[CH:4]=1

Participants

4

Reactant 1

HCID 22789124HCID 22789124, compound

Product 1

HCID 22789125HCID 22789125, compound

Reagents, catalysts & solvents 2

HCID 12000666Calcium Palladium CarbonateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

700 mg. pf rac.-1,3-dimethoxy-17β-acetoxy-1,3,5(10),8,14-estrapentaene in 10 ml. of distilled THF is hydrogenated over 200 mg. Pd/CaCO3 (5%) at room temperature and under normal pressure until 46.6 ml. of H2 has been absorbed. After the mixture has been filtered off from the catalyst, dried, and evaporated, 447 mg. of rac.-1,3-dimethoxy-17β-acetoxy-1,3,5(10),8-esratetraene is obtained from methanol, m.p. 111/112°-113° C.

Workup

  1. customat room temperature
  2. customof H2 has been absorbed
  3. filtrationAfter the mixture has been filtered off from the catalyst
  4. customdried
  5. customevaporated
  6. customof rac.-1,3-dimethoxy-17β-acetoxy-1,3,5(10),8-esratetraene is obtained from methanol
  7. custom112°-113° C.

Sources & evidence

ORD record
ord-f9d9482f2d21437b9001a9725a6d04da
Source dataset
uspto-grants-1976_04
Patent number
US03951959

Reaction notes

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