Water → HCID 70505471, compound

HRID 2418143Notes

Reaction equation

HRID 2418143 reaction equation
[OH:1][C@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C:4](=[CH:5][CH2:6][C@@H:7]3[C@@H:16]2[CH2:15][CH2:14][C@@:12]2([CH3:13])[C@H:8]3[C@@H:9]3[CH2:22][C@@H:10]3[C:11]2=[O:21])[CH2:3]1.[C:23](Cl)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.O>N1C=CC=CC=1.C(Cl)Cl>[C:23]([O:1][C@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C:4](=[CH:5][CH2:6][C@@H:7]3[C@@H:16]2[CH2:15][CH2:14][C@@:12]2([CH3:13])[C@H:8]3[C@@H:9]3[CH2:22][C@@H:10]3[C:11]2=[O:21])[CH2:3]1)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 3

HCID 962WaterHCID 7412Benzoyl chlorideHCID 1307594967372-65-0

Product 1

HCID 70505471HCID 70505471, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 5.0 g of 3β-hydroxy-15β,16β-methylene-5-androsten-17-one in 50 ml of pyridine was combined under ice cooling with 5 ml of benzoyl chloride and then stirred for 17 hours at room temperature. After the addition of 10 ml of water, the mixture was stirred for another hour; then the reaction solution was diluted with methylene chloride and washed with sodium carbonate solution and water. After drying and evaporation, the residue was triturated with diisopropyl ether and vacuum-filtered, thus obtaining 6.4 g of 3β-benzoyloxy-15β,16β-methylene-5-androsten-17-one, mp 250°-258° C.

Workup

  1. stirringthe mixture was stirred for another hour
  2. washwashed with sodium carbonate solution and water
  3. customAfter drying
  4. customevaporation
  5. customthe residue was triturated with diisopropyl ether
  6. filtrationvacuum-filtered

Sources & evidence

ORD record
ord-420ed9d9aef647808eb71a6a51a8fca1
Source dataset
uspto-grants-1984_09
Patent number
US04472310

Reaction notes

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