Hydrochloric Acid → HCID 53923971, compound

HRID 1196833Notes

Reaction equation

HRID 1196833 reaction equation
O1CCCCC1[O:7][C@H:8]1[CH2:13][CH2:12][C@H:11]2[C@H:14]3[C@H:23]([CH2:24][CH2:25][C@:9]12[CH3:10])[C@@H:22]1[C@H:17]([CH2:18][CH:19]=[CH:20][CH2:21]1)[CH2:16][CH2:15]3.Cl.O.CCOCC>CO>[OH:7][C@H:8]1[CH2:13][CH2:12][C@H:11]2[C@H:14]3[C@H:23]([CH2:24][CH2:25][C@:9]12[CH3:10])[C@@H:22]1[C@H:17]([CH2:18][CH:19]=[CH:20][CH2:21]1)[CH2:16][CH2:15]3

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3283Diethyl EtherHCID 22844095HCID 22844095, compound2×

Product 1

HCID 53923971HCID 53923971, compoundYield 100.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 0.25 g of 17β-tetrahydropyranyloxy-5α-estr-2-en, Compound 4, in 8 ml of methanol is added 1N hydrochloric acid (0.2 ml) and the reaction mixture is stirred at room temperature for 6 hr. Evaporation of the solvent under vacuum produces a residue of white crystals. The residue is treated with water (15 ml) and ether (25 ml). The ether phase is separated, and the water is extracted once more with 12 ml of ether. The combined ether phase is washed with water, sodium chloride solution, and dried over sodium sulfate. Evaporation of the solvent produces 0.19 g of 17β-hydroxy-5α-estr-2-ene. The structure of the Compound 5, is confirmed by the following spectral data:

Workup

  1. customEvaporation of the solvent under vacuum
  2. customproduces a residue of white crystals
  3. customThe ether phase is separated
  4. extractionthe water is extracted once more with 12 ml of ether
  5. washThe combined ether phase is washed with water, sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. customEvaporation of the solvent

Sources & evidence

ORD record
ord-b6814353ae364312a188e30f143939af
Source dataset
uspto-grants-1992_05
Patent number
US05116830

Reaction notes

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