Dimethylformamide → HCID 70376628, compound

HRID 1382731Notes

Reaction equation

HRID 1382731 reaction equation
[C:1]([O:4][C@H:5]1[CH2:10][CH2:9][C@H:8]2[C@H:11]3[C@H:20]([CH2:21][CH2:22][C@:6]12[CH3:7])[C:19]1C[CH2:17][C:16]2([O:26][CH2:25][CH2:24][O:23]2)[CH2:15][C:14]=1[CH2:13][CH2:12]3)(=[O:3])[CH3:2].C([O-])([O-])=O.[Ca+2].[Br:32]N1C(=O)CCC1=O.CN(C)[CH:42]=[O:43]>O>[C:1]([O:4][C@H:5]1[CH2:10][CH2:9][C@H:8]2[C@H:11]3[C@H:20]([CH2:21][CH2:22][C@:6]12[CH3:7])[C@:19]1([Br:32])[C@:42]([OH:43])([CH2:17][C:16]2([O:26][CH2:25][CH2:24][O:23]2)[CH2:15][CH2:14]1)[CH2:13][CH2:12]3)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10112Calcium CarbonateHCID 67184N-bromobutanimideHCID 10642279HCID 10642279, compound

Product 1

HCID 70376628HCID 70376628, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of 8.5 g of 17β-acetoxy-3,3-ethylenedioxy-estr-5(10)-ene in 130 ml of dimethylformamide and 40 ml of water, 2.35 g of powdered CaCO3 and 8.39 g of N-bromosuccinimide are added at room temperature. After stirring for 4 hours at room temperature, the yellow suspension is poured into ice-water and the precipitate filtered on buckner; the precipitate is dissolved in methylene chloride and the insoluble residue is filtered off; the filtrate is washed with water and dried over anhydrous sodium sulphate. Evaporation of the solvent yields 10.7 g of 17β-acetoxy-3,3-ethylenedioxy-5α-hydroxy-10β-bromo-estrane as a white solid material,

Workup

  1. additionare added at room temperature
  2. filtrationthe precipitate filtered on buckner
  3. dissolutionthe precipitate is dissolved in methylene chloride
  4. filtrationthe insoluble residue is filtered off
  5. washthe filtrate is washed with water
  6. dry with materialdried over anhydrous sodium sulphate
  7. customEvaporation of the solvent

Sources & evidence

ORD record
ord-9c6337e3fa8f4fa687ad2f26ed1b7238
Source dataset
uspto-grants-1989_02
Patent number
US04808578

Reaction notes

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