Dichloromethane → HCID 18600043, compound

HRID 1583260Notes

Reaction equation

HRID 1583260 reaction equation
[CH3:1][O:2][C:3]1[CH2:20][CH2:19][C@@:18]2([CH3:21])[C:5](=[CH:6][CH2:7][C@@H:8]3[C:17]2=[CH:16][CH2:15][C@@:13]2([CH3:14])[C@H:9]3[CH2:10][CH2:11][C:12]2=[C:22]([N+:33]#[C-:34])[S:23]([C:26]2[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=2)(=[O:25])=[O:24])[CH:4]=1.[OH-].[Na+].[CH2:37](Cl)[Cl:38]>[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C>[CH3:1][O:2][C:3]1[CH2:20][CH2:19][C@@:18]2([CH3:21])[C:5](=[CH:6][CH2:7][C@@H:8]3[C:17]2=[CH:16][CH2:15][C@@:13]2([CH3:14])[C@H:9]3[CH2:10][CH:11]=[C:12]2[C:22]([N+:33]#[C-:34])([S:23]([C:26]2[CH:27]=[CH:28][C:29]([CH3:32])=[CH:30][CH:31]=2)(=[O:25])=[O:24])[CH2:37][Cl:38])[CH:4]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 54027489HCID 54027489, compound

Product 1

HCID 18600043HCID 18600043, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 66133Benzyl triethylammonium chlorideCatalyst

Procedure

3-Methoxy-17-(isocyano-p-methylphenylsulfonylmethylene)-androsta-3,5,9(11)-triene (476 mg, 1.00 mmol) and triethylbenzylammonium chloride (20 mg) were dissolved in methylene chloride (10 ml). After stirring for 2 hours at 25° C. with a sodium hydroxide solution (5 ml, 50%), the organic layer was seperated and dried over Na2SO4, followed by filtration over alumina (act. II-III). Evaporation of the solvent afforded the title compound (368 mg, 70%).

Workup

  1. customthe organic layer was seperated
  2. dry with materialdried over Na2SO4
  3. filtrationfollowed by filtration over alumina (act. II-III)
  4. customEvaporation of the solvent

Sources & evidence

ORD record
ord-d33a1bb6676d4a7ba0cfa2ef116e7f79
Source dataset
uspto-grants-1985_11
Patent number
US04551278

Reaction notes

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