Water → HCID 10334868, compound

HRID 2219063Notes

Reaction equation

HRID 2219063 reaction equation
[I-].[C:2]1(C([PH3+])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[H-].[Na+].[OH:24][C:25]1[CH:42]=[CH:41][C:40]2[C@:39]3([CH:43]=O)[C@H:30]([C@H:31]4[C@@:35]([CH2:37][CH2:38]3)([CH3:36])[CH2:34][C@H:33]([OH:45])[CH2:32]4)[CH2:29][CH2:28][C:27]=2[CH:26]=1.O>CS(C)=O>[CH:43]([C@:39]12[CH2:38][CH2:37][C@@:35]3([CH3:36])[C@@H:31]([CH2:32][C@@H:33]([OH:45])[CH2:34]3)[C@@H:30]1[CH2:29][CH2:28][C:27]1[CH:26]=[C:25]([OH:24])[CH:42]=[CH:41][C:40]2=1)=[CH2:2]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 12095978HCID 12095978, compoundHCID 66599960Tritylphosphanium iodide

Product 1

HCID 10334868HCID 10334868, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Under inert-gas atmosphere, 3.1 g (7.9 mmol) of triphenylmethyl phosphonium iodide and 0.24 g (8 mmol) of sodium hydride (80% in paraffin oil) in 20 ml of DMSO in an ultrasound bath are brought to reaction at about 55° C. After 10 minutes, 80 mg (0.16 mmol, about 60%) of 3,16α-dihydroxyestra-1,3,5(10)-triene-9 carbaldehyde is added to the solution, and the mixture is allowed to react for 60 more minutes at about 55° C. in an ultrasound bath. After water is added, it is extracted with ethyl acetate. The collected organic phases are washed with water, and the organic phase is concentrated by evaporation in a vacuum.

Workup

  1. customto react for 60 more minutes at about 55° C. in an ultrasound bath
  2. extractionit is extracted with ethyl acetate
  3. washThe collected organic phases are washed with water
  4. concentrationthe organic phase is concentrated by evaporation in a vacuum

Sources & evidence

ORD record
ord-c8953e5a7bae47da85658f7ddd4aae78
Source dataset
uspto-grants-2008_08
Patent number
US07414043B2

Reaction notes

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