Methanol → HCID 22295513, compound

HRID 1587024Notes

Reaction equation

HRID 1587024 reaction equation
C([O:4][C@@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C@H:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:19]2[CH2:18][C@H:17]([O:24]C(=O)C)[C@@:15]2([CH3:16])[C@H:11]3[CH2:12][CH2:13][C:14]2=[O:28])[CH2:6]1)(=O)C.O.[OH-].[Li+].CO.O1CCCC1>C(OCC)(=O)C.O>[OH:4][C@@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C@H:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:19]2[CH2:18][C@H:17]([OH:24])[C@@:15]2([CH3:16])[C@H:11]3[CH2:12][CH2:13][C:14]2=[O:28])[CH2:6]1

Participants

7

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 224449HCID 224449, compound

Product 1

HCID 22295513HCID 22295513, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3α, 12α-diacetoxy-5β-androstan-17-one (5.5 g) and lithium hydroxide monohydrate (1.7 g) in a solution of methanol (20 ml), tetrahydrofuran (20 ml) and water (20 ml) is stirred at room temperature for about two hours, diluted with ethyl acetate and washed three times with water. The organic solution is dried over magnesium sulfate, filtered and concentrated in vacuo. Benzene is azeotroped from the residue to give the desired product which is used, without further treatment, for the next step.

Workup

  1. washwashed three times with water
  2. dry with materialThe organic solution is dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customBenzene is azeotroped from the residue

Sources & evidence

ORD record
ord-6d64cfe780e44d1a8c1d612370d679ad
Source dataset
uspto-grants-1993_06
Patent number
US05216015

Reaction notes

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