Hydrochloric Acid → HCID 68143785, compound

HRID 1077187Notes

Reaction equation

HRID 1077187 reaction equation
Cl.CO.[CH2:4]([C@:8]12[CH2:16][CH2:15][C@@H:14]3[C:17]4[CH2:18][CH:19]=[C:20]([O:25]C)[CH2:21][C:22]=4[CH2:23][CH2:24][C@H:13]3[C@@H:12]1[CH2:11][CH2:10][C@@H:9]2[OH:27])[CH:5]([CH3:7])[CH3:6]>O>[CH2:4]([C@:8]12[CH2:16][CH2:15][C@@H:14]3[C@@H:17]4[C:22]([CH2:23][CH2:24][C@H:13]3[C@@H:12]1[CH2:11][CH2:10][C@@H:9]2[OH:27])=[CH:21][C:20](=[O:25])[CH2:19][CH2:18]4)[CH:5]([CH3:7])[CH3:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 68144281HCID 68144281, compound

Product 1

HCID 68143785HCID 68143785, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Add to a mixture of concentrated hydrochloric acid (4.8 cc.), water (3.2 cc.) and methanol (.72 cc.) 13β-isobutyl-3-methoxy-gona-2,5(10)-dien-17β-ol (2.0 g.). Heat the resulting solution on a steam bath for 30 minutes with stirring. Cool to room temperature, dilute the solution with water (160 cc.) and extract with ether. Wash the ethereal solution with water, sodium bicarbonate, and water, dry over anhydrous sodium sulfate. Filter and remove the solvent under reduced pressure to give a gum. Recrystallize from ethyl acetate to obtain the title compound (0.8 g., 43%, m.p. 124.0°-125.5°; ultraviolet absorption peak at 240 mμ (ε18,200).

Workup

  1. temperatureHeat the resulting solution on a steam bath for 30 minutes
  2. extractionextract with ether
  3. washWash the ethereal solution with water, sodium bicarbonate, and water
  4. dry with materialdry over anhydrous sodium sulfate
  5. filtrationFilter
  6. customremove the solvent under reduced pressure
  7. customto give a gum
  8. customRecrystallize from ethyl acetate

Sources & evidence

ORD record
ord-f1a60db4ae4c45959097d8fc9fa631d3
Source dataset
uspto-grants-1976_05
Patent number
US03959322

Reaction notes

Loading…