Phosphorus oxychloride → HCID 66858598, compound

HRID 1661130Notes

Reaction equation

HRID 1661130 reaction equation
P(Cl)(Cl)(Cl)=O.[CH2:6]([O:13][C:14]1[CH:31]=[CH:30][C:29]2[C@@H:28]3[C@H:19]([C@H:20]4[C@@:24]([CH2:26][CH2:27]3)([CH3:25])[C:23](O)([C:32]([F:35])([F:34])[F:33])[CH2:22][CH:21]4[CH2:37][CH2:38][CH2:39][CH2:40][O:41][C:42](=[O:47])[C:43]([CH3:46])([CH3:45])[CH3:44])[CH2:18][CH2:17][C:16]=2[CH:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>N1C=CC=CC=1>[CH2:6]([O:13][C:14]1[CH:31]=[CH:30][C:29]2[C@@H:28]3[C@H:19]([C@H:20]4[C@@:24]([CH2:26][CH2:27]3)([CH3:25])[C:23]([C:32]([F:34])([F:35])[F:33])=[CH:22][CH:21]4[CH2:37][CH2:38][CH2:39][CH2:40][O:41][C:42](=[O:47])[C:43]([CH3:46])([CH3:45])[CH3:44])[CH2:18][CH2:17][C:16]=2[CH:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 66859795HCID 66859795, compound

Product 1

HCID 66858598HCID 66858598, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Phosphorylchloride (0.25 ml; 200 μmol) was added to a solution of 2,2-Dimethylpropionic acid 4-(3-benzyloxy-17-hydroxy-17-trifluoromethyl-estra-1,3,5(10)-trien-15-yl)-butylester (80.0 mg; 136 μmol) in pyridine (2.50 ml) and the resulting mixture is heated under reflux for 24 h. Then, the mixture was allowed to cool to RT, diluted with ice water and extracted with ether. The combined organic phases were dried over MgSO4 and the solvent was evaporated. The residue was purified by column chromatography (SiO2, DCM) yielding the title compound (60.0 mg, 78%) as colourless oil.

Workup

  1. temperaturethe resulting mixture is heated
  2. temperatureunder reflux for 24 h
  3. extractionextracted with ether
  4. dry with materialThe combined organic phases were dried over MgSO4
  5. customthe solvent was evaporated
  6. customThe residue was purified by column chromatography (SiO2, DCM)

Sources & evidence

ORD record
ord-7de2e3e71c3241ceaae107a7087997e6
Source dataset
uspto-grants-2011_10
Patent number
US08030298B2

Reaction notes

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