Hydrochloric Acid → HCID 69997935, compound

HRID 566886Notes

Reaction equation

HRID 566886 reaction equation
[C:1]([O:9][C@H:10]1[CH2:37][CH2:36][C@@:35]2([CH3:38])[C:12](=[CH:13][CH:14]=[C:15]3[C@@H:34]2[CH2:33][CH2:32][C@@:31]2([CH3:39])[C@H:16]3[CH2:17][CH2:18][C@@H:19]2[C@H:20]([CH3:30])[CH2:21][O:22][Si](C(C)(C)C)(C)C)[C:11]1([CH3:41])[CH3:40])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC=CC=1.Cl.C(=O)([O-])O.[Na+]>C(O)C>[C:1]([O:9][C@H:10]1[CH2:37][CH2:36][C@@:35]2([CH3:38])[C@@H:12]([CH2:13][CH2:14][C:15]3[C:16]4[C@:31]([CH3:39])([CH2:32][CH2:33][C:34]=32)[C@@H:19]([C@H:20]([CH3:30])[CH2:21][OH:22])[CH2:18][CH:17]=4)[C:11]1([CH3:40])[CH3:41])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 516892Sodium BicarbonateHCID 70167450HCID 70167450, compound

Product 1

HCID 69997935HCID 69997935, compoundYield 67.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

vii)—A mixture of compound 8 (32.3 g), toluene (84 ml), ethanol (96%; 588 ml) and concentrated hydrochloric acid (84 ml) was heated under reflux for 3 h. The mixture was cooled and poured into a saturated aqueous solution of sodium hydrogen carbonate (1 l). The product was extracted into ethyl acetate; the combined organic phases were washed with brine, dried over sodium sulfate, and concentrated under reduced pressure. Column chromatography afforded a 3:1 mixture (17.4 g) of (3β,5α,20S)-4,4,20-trimethylpregna-8,14-diene-3,21-diol 3-benzoate (9) and (3β,5α,20S)-4,4,20-trimethylpregna-6,8(14)-diene-3,21-diol 3-benzoate. The mixture was used as such in the next step.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 h
  3. temperatureThe mixture was cooled
  4. extractionThe product was extracted into ethyl acetate
  5. washthe combined organic phases were washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-03143962642c4db293cbf47c6e3936f3
Source dataset
uspto-grants-2001_01
Patent number
US06177420B1

Reaction notes

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