Hydrochloric Acid → HCID 15237328, compound

HRID 1741679Notes

Reaction equation

HRID 1741679 reaction equation
[ClH:1].O[C@@H:3]1[CH2:7][CH2:6][CH2:5][C@H:4]1[S:8][CH2:9][C:10]([OH:12])=[O:11].[Cl-].[Na+]>O>[Cl:1][C@@H:3]1[CH2:7][CH2:6][CH2:5][C@H:4]1[S:8][CH2:9][C:10]([OH:12])=[O:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 53890201HCID 53890201, compound

Product 1

HCID 15237328HCID 15237328, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Concentrated hydrochloric acid (50 ml) was added to the product of Example 3 (8.4 g) and stirred for 20 hours at room temperature. The reaction mixture was poured into a solution of water (50 ml) containing sodium chloride and extracted three times with 75 ml of diethyl ether. The combined diethyl ether extracts were dried over anhydrous magnesium sulfate, filtered and concentrated to an oil with a rotary evaporator. The product was purified by silica gel chromatography, and the structure was supported by NMR spectroscopy. The NMR spectrum showed a small amount of the cis-product as well.

Workup

  1. extractionextracted three times with 75 ml of diethyl ether
  2. dry with materialThe combined diethyl ether extracts were dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated to an oil with a rotary evaporator
  5. customThe product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-cea7eee7d8a84c5584397dfff5bf0ff6
Source dataset
uspto-grants-1994_08
Patent number
US05334616

Reaction notes

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