Allyl bromide → HCID 70400685, compound

HRID 371053Notes

Reaction equation

HRID 371053 reaction equation
[F:1][C@:2]12[C@@H:19]([OH:20])[CH2:18][C@@:16]3([CH3:17])[C@@H:12]([CH2:13][CH2:14][C@@H:15]3[SH:21])[C@@H:11]1[CH2:10][CH2:9][C:8]1[C@:3]2([CH3:23])[CH:4]=[CH:5][C:6](=[O:22])[CH:7]=1.[OH-].[Na+].[CH2:26](Br)[CH:27]=[CH2:28]>CO>[F:1][C@:2]12[C@@H:19]([OH:20])[CH2:18][C@@:16]3([CH3:17])[C@@H:12]([CH2:13][CH2:14][C@@H:15]3[S:21][CH2:28][CH:27]=[CH2:26])[C@@H:11]1[CH2:10][CH2:9][C:8]1[C@:3]2([CH3:23])[CH:4]=[CH:5][C:6](=[O:22])[CH:7]=1

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 14798Sodium HydroxideHCID 86740191HCID 86740191, compound

Product 1

HCID 70400685HCID 70400685, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 1.7 g of (11β,17β)-9-Fluoro-11-hydroxy-17-mercaptoandrosta-1,4-dien-3-one dissolved in 100 ml of methanol, there was added 1 g of sodium hydroxide followed by 2.5 ml of allyl bromide (nitrogen atmosphere). The alkylation was complete after 1 hour of stirring at room temperature. The solution was partly evaporated, water was added and the resulting solid filtered and washed with water. Crystallization of the solid from ethyl acetate-petroleum ether furnished 1.08 g of the analytical sample, melting point 173°-175° C.

Workup

  1. customThe solution was partly evaporated
  2. additionwater was added
  3. filtrationthe resulting solid filtered
  4. washwashed with water
  5. customCrystallization of the solid from ethyl acetate-petroleum ether
  6. customfurnished 1.08 g of the analytical sample, melting point 173°-175° C.

Sources & evidence

ORD record
ord-1a77b9a2737c4e80985fc56b47827dab
Source dataset
uspto-grants-1985_07
Patent number
US04529548

Reaction notes

Loading…