Sodium Hydroxide → HCID 69104800, compound

HRID 2224042Notes

Reaction equation

HRID 2224042 reaction equation
[C-:1]#[N:2].C([Al+]CC)C.[CH3:8][O:9][C:10]1[CH:27]=[CH:26][C:25]2[C:24]3[C:23](=[O:28])[CH2:22][C@@:20]4([CH3:21])[C@@H:16]([CH2:17][CH2:18][C@@H:19]4[O:29][CH:30]4[CH2:35][CH2:34][CH2:33][CH2:32][O:31]4)[C:15]=3[CH2:14][CH2:13][C:12]=2[CH:11]=1.[OH-].[Na+]>C1(C)C=CC=CC=1>[C:1]([C@@:15]12[CH2:14][CH2:13][C:12]3[CH:11]=[C:10]([O:9][CH3:8])[CH:27]=[CH:26][C:25]=3[C@H:24]1[C:23](=[O:28])[CH2:22][C@@:20]1([CH3:21])[C@H:16]2[CH2:17][CH2:18][C@@H:19]1[O:29][CH:30]1[CH2:35][CH2:34][CH2:33][CH2:32][O:31]1)#[N:2]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 15907968HCID 15907968, compoundHCID 16686413Diethyl aluminum cyanide

Product 1

HCID 69104800HCID 69104800, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

195 ml of diethylaluminum cyanide (1.0 M, in toluene) was added in drops at a temperature of −5° C. under argon to a solution of 24.5 g of 11-ketosteroid 2 in 330 ml of toluene, and it was stirred for 1.5 hours while cooling was continued. Then, the mixture was poured onto 470 ml of ice-cooled 1N sodium hydroxide solution, stirred for 1 hour, extracted several times with ethyl acetate, and the collected organic phases were washed with water and brine and dried with magnesium sulfate. The chromatography of the evaporation residue on silica gel (solvent mixture: cyclohexane/ethyl acetate=4/1) yielded 3 as a foam in a yield of a total of 12.0 g (37%).

Workup

  1. temperaturewhile cooling
  2. stirringstirred for 1 hour
  3. extractionextracted several times with ethyl acetate
  4. washthe collected organic phases were washed with water and brine
  5. dry with materialdried with magnesium sulfate

Sources & evidence

ORD record
ord-b5cc30c2488e49e9bf396e9218b8122b
Source dataset
uspto-grants-2008_05
Patent number
US07378404B2

Reaction notes

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