Lithium Hydroxide → HCID 15513564, compound

HRID 968187Notes

Reaction equation

HRID 968187 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:9][C:10]1[CH:27]=[CH:26][C:25]2[C@@H:24]3[C@H:15]([C@H:16]4[C@@:20]([CH2:22][CH2:23]3)([CH3:21])[C:19](=[O:28])[CH2:18][CH2:17]4)[C@@H:14]([OH:29])[CH2:13][C:12]=2[CH:11]=1.[OH-].[Li+]>CN(C)C=O>[CH2:1]([O:9][C:10]1[CH:27]=[CH:26][C:25]2[C@@H:24]3[C@H:15]([C@H:16]4[C@@:20]([CH2:22][CH2:23]3)([CH3:21])[C:19](=[O:28])[CH2:18][CH2:17]4)[C@@H:14]([OH:29])[CH2:13][C:12]=2[CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 7498Benzyl BromideHCID 9921948HCID 9921948, compound

Product 1

HCID 15513564HCID 15513564, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

12.83 g (75 mmol) of benzylbromide is added to a suspension of 20 g (67.74 mmol) of 3,7β-dihydroxy-estra-1,3,5(10)-trien-17-one, 3.55 g (148.23 mmol) of lithium hydroxide in 700 ml of dry dimethylformamide, and it is stirred under an argon atmosphere for 30 minutes at 100° C. For working-up, the reaction solution is poured into tartaric-acid ice water, the precipitated product is suctioned off and dried in air. The crude product is taken up in dichloromethane, the organic phase is washed with water and dried on sodium sulfate. After the solvent is drawn off in a vacuum, it is chromatographed on silica gel (dichloromethane-ethyl acetate, gradient of up to 3:2), yield 22.81 g (87%).

Workup

  1. customdried in air
  2. washthe organic phase is washed with water
  3. customdried on sodium sulfate
  4. customis chromatographed on silica gel (dichloromethane-ethyl acetate, gradient of up to 3:2), yield 22.81 g (87%)

Sources & evidence

ORD record
ord-ae16440e0965494cb8ffddf5826a3ead
Source dataset
uspto-grants-2005_10
Patent number
US06958327B1

Reaction notes

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