Hydrochloric Acid → HCID 69789703, compound

HRID 1815788Notes

Reaction equation

HRID 1815788 reaction equation
[CH2:1]([C@H:3]1[CH2:20][C@@:18]2([CH3:19])[C@H:14]([CH2:15][CH2:16][C@H:17]2[CH2:21][OH:22])[C@H:13]2[C@H:4]1[C:5]1[CH2:6][CH:7]=[C:8]([O:23]C)[CH2:9][C:10]=1[CH2:11][CH2:12]2)[CH3:2].Cl.C(=O)([O-])O.[Na+].O>O1CCCC1>[CH2:1]([C@H:3]1[CH2:20][C@@:18]2([CH3:19])[C@H:14]([CH2:15][CH2:16][C@H:17]2[CH2:21][OH:22])[C@H:13]2[C@H:4]1[C:5]1[CH2:6][CH2:7][C:8](=[O:23])[CH2:9][C:10]=1[CH2:11][CH2:12]2)[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 516892Sodium BicarbonateHCID 69789910HCID 69789910, compound

Product 1

HCID 69789703HCID 69789703, compoundYield 104.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

xi)—A solution of (11β,14β,17α)-11-ethyl-3-methoxyestra-2,5(10)-diene-17-methanol (3.3 g) in tetrahydrofuran (30 ml) was treated with hydrochloric acid (2 M, 10 ml). The reaction mixture was stirred at room temperature for 30 min. and then neutralized with a saturated aqueous solution of sodium hydrogencarbonate. Water was added and the product was extracted into ethyl acetate. The combined organic phases were washed with brine, dried over sodium sulfate and concentrated under reduced pressure, to give (11β,14β,17α)-11-ethyl-17-(hydroxymethyl)estr-5(10)-en-3-one (3.3 g). The product was used in the following step without further purification.

Workup

  1. extractionthe product was extracted into ethyl acetate
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3cb3e8d18c9a454db11d1b7441c39e79
Source dataset
uspto-grants-2005_04
Patent number
US06881728B1

Reaction notes

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