Benzyl Bromide → HCID 69334435, compound

HRID 1003189Notes

Reaction equation

HRID 1003189 reaction equation
[OH:1][C:2]1[C:19]([N+:20]([O-:22])=[O:21])=[CH:18][C:17]2[C@@H:16]3[C@H:7]([C@H:8]4[C@@:12]([CH2:14][CH2:15]3)([CH3:13])[C:11](=[O:23])[CH2:10][CH2:9]4)[CH2:6][CH2:5][C:4]=2[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:30](Br)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.[NH4+].[Cl-]>CN(C=O)C>[CH2:30]([O:1][C:2]1[C:19]([N+:20]([O-:22])=[O:21])=[CH:18][C:17]2[C@@H:16]3[C@H:7]([C@H:8]4[C@@:12]([CH2:14][CH2:15]3)([CH3:13])[C:11](=[O:23])[CH2:10][CH2:9]4)[CH2:6][CH2:5][C:4]=2[CH:3]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 2334963-Hydroxy-2-nitroestra-1(10),2,4-trien-17-one

Product 1

HCID 69334435HCID 69334435, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-hydroxy-2-nitroestra-1,3,5(10)-trien-17-one (76b, 1.58 g, 5.0 mmol) in DMF (20 mL) were added potassium carbonate (1.38 g, 10 mmol) and benzyl bromide (0.9 mL, 7.5 mmol) and stirred for 19 h at room temperature. To the reaction mixture was added saturated aqueous NH4Cl at 0° C. and extracted with CHCl3. The combined organic layers were washed with H2O, saturated aqueous NaCl, and then dried (Na2SO4). The desiccant was filtered and the solvent was evaporated at reduced pressure. The residue was washed with Et2O to afford 2.01 g of 79 (99% yield) mp: 234-235° C.

Workup

  1. extractionextracted with CHCl3
  2. washThe combined organic layers were washed with H2O, saturated aqueous NaCl
  3. dry with materialdried (Na2SO4)
  4. filtrationThe desiccant was filtered
  5. customthe solvent was evaporated at reduced pressure
  6. washThe residue was washed with Et2O

Sources & evidence

ORD record
ord-6a13a30ca65b420c87bf8d45ddb81421
Source dataset
uspto-grants-2000_04
Patent number
US06046186

Reaction notes

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