Water → 1-Acetoxy-16beta-chloro-3-methoxyestra-1,3,5(10)-trien-17-one

HRID 839756Notes

Reaction equation

HRID 839756 reaction equation
[Cl-:1].[Li+].[C:3]([O:6][C:7]1[C:24]2[C@@H:23]3[C@H:14]([C@H:15]4[C@@:19]([CH2:21][CH2:22]3)([CH3:20])[C:18](=[O:25])[C@H:17](Br)[CH2:16]4)[CH2:13][CH2:12][C:11]=2[CH:10]=[C:9]([O:27][CH3:28])[CH:8]=1)(=[O:5])[CH3:4].O>CN(C)C=O>[C:3]([O:6][C:7]1[C:24]2[C@@H:23]3[C@H:14]([C@H:15]4[C@@:19]([CH2:21][CH2:22]3)([CH3:20])[C:18](=[O:25])[C@@H:17]([Cl:1])[CH2:16]4)[CH2:13][CH2:12][C:11]=2[CH:10]=[C:9]([O:27][CH3:28])[CH:8]=1)(=[O:5])[CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 433294Lithium ChlorideHCID 706146041-Acetoxy-16alpha-bromo-3-methoxyestra-1,3,5(10)-trien-17-one

Product 1

HCID 706144451-Acetoxy-16beta-chloro-3-methoxyestra-1,3,5(10)-trien-17-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of lithium chloride (1.3 g, 31 mM) in 9 ml of anhydrous dimethylformamide is heated to 70° and then cooled to room temperature. 1-Acetoxy-16α-bromo-3-methoxyestra-1,3,5(10)-trien-17-one (0.50 g) is added to the solution as a solid using Gooch tubing. The resulting suspension is heated to 50° to effect solution. The solution is then stirred at room temperature for 5 hr, poured into 100 ml of H2O, filtered and dried in vacuo to give a white solid. Recrystallization from methanol gives 1-acetoxy-16β-chloro-3-methoxyestra-1,3,5(10)-trien-17-one, yield 0.40 g (89%); m.p. 164°-166°.

Workup

  1. temperatureThe resulting suspension is heated to 50°
  2. filtrationfiltered
  3. customdried in vacuo
  4. customto give a white solid
  5. customRecrystallization from methanol

Sources & evidence

ORD record
ord-8ec2197b439f4a239bf154129042e336
Source dataset
uspto-grants-1978_06
Patent number
US04096253

Reaction notes

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