Chloride → 17beta-Benzoyloxy-5alpha-androstan-4-one

HRID 354915Notes

Reaction equation

HRID 354915 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:10][C@H:11]1[CH2:16][CH2:15][C@H:14]2[C@H:17]3[C@H:27]([CH2:28][CH2:29][C@:12]12[CH3:13])[C@:25]1([CH3:26])[C@H:20]([C:21](=[O:30])[CH2:22][CH2:23][CH2:24]1)[CH2:19][CH2:18]3.[Cl-]>N1C=CC=CC=1>[C:1]([O:10][C@H:11]1[CH2:16][CH2:15][C@H:14]2[C@H:17]3[C@H:27]([CH2:28][CH2:29][C@:12]12[CH3:13])[C@:25]1([CH3:26])[C@H:20]([C:21](=[O:30])[CH2:22][CH2:23][CH2:24]1)[CH2:19][CH2:18]3)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 312ChlorideHCID 7412Benzoyl chlorideHCID 15341898HCID 15341898, compound

Product 1

HCID 1534189917beta-Benzoyloxy-5alpha-androstan-4-one

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 12 ml of dry pyridine and 6 ml of benzoyl chloride is added 2.0 g of the product of Step F to form a solution which is heated on a steam bath for 30 min. and then poured into 175 ml of ice water and stirred to decompose the excess chloride. The reaction mixture is filtered, washed with water, and pumped dry under high vacuum at 50° C. to yield 1.7 g of final product.

Workup

  1. customto form a solution which
  2. temperatureis heated on a steam bath for 30 min.
  3. filtrationThe reaction mixture is filtered
  4. washwashed with water
  5. custompumped dry under high vacuum at 50° C.

Sources & evidence

ORD record
ord-20eaecd6abc74531a2c2484020935134
Source dataset
uspto-grants-1983_03
Patent number
US04377584

Reaction notes

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