Hydrochloric Acid → HCID 54465838, compound

HRID 436285Notes

Reaction equation

HRID 436285 reaction equation
[C:1]([O:32]C)(=[O:31])[CH2:2][CH2:3][C:4]([O:6][CH2:7][C:8]([CH3:30])([CH3:29])[O:9][C:10]1[CH:11]=[CH:12][C:13]2[C:14]3[C:22]([CH2:23][CH2:24][C:25]=2[CH:26]=1)=[C:21]1[C:17]([C:18]([CH3:28])([CH3:27])[CH2:19][CH2:20]1)=[CH:16][CH:15]=3)=[O:5].[I-].[Li+].Cl>N1C=CC=CC=1>[C:4]([O:6][CH2:7][C:8]([CH3:30])([CH3:29])[O:9][C:10]1[CH:11]=[CH:12][C:13]2[C:14]3[C:22]([CH2:23][CH2:24][C:25]=2[CH:26]=1)=[C:21]1[C:17]([C:18]([CH3:28])([CH3:27])[CH2:19][CH2:20]1)=[CH:16][CH:15]=3)(=[O:5])[CH2:3][CH2:2][C:1]([OH:32])=[O:31]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 66321Lithium iodideHCID 86734497HCID 86734497, compound

Product 1

HCID 54465838HCID 54465838, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 7 parts of methyl 2,2-dimethyl-2-[(7,15,16,17-tetrahydro-17,17-dimethyl-6H-cyclopenta[a]phenanthren-3-yl)oxy]ethyl butanedioate and 24 parts of lithium iodide in 700 parts of pyridine is heated at the boiling point under reflux for 3 days, then cooled and thereupon poured into 1000 parts of approximately 4% hydrochloric acid. The resultant mixture is extracted with dichloromethane. The dichloromethane extract is consecutively washed with 4% hydrochloric acid and water, dried over anhydrous sodium sulfate, and stripped of solvent by vacuum distillation. The residue is crystallized from a mixture of ether and hexane to give 2,2-dimethyl-2-[(7,15,16,17-tetrahydro-17,17-dimethyl-6H-cyclopenta[a]phenanthren-3-yl)oxy]ethyl hydrogen butanedioate melting at 118°-120°. The product has the formula ##STR10##

Workup

  1. temperatureis heated at the boiling point
  2. temperatureunder reflux for 3 days
  3. temperaturecooled
  4. extractionThe resultant mixture is extracted with dichloromethane
  5. extractionThe dichloromethane extract
  6. washis consecutively washed with 4% hydrochloric acid and water
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationstripped of solvent by vacuum distillation
  9. customThe residue is crystallized from a mixture of ether and hexane

Sources & evidence

ORD record
ord-f5f3d6063c9144a08734da747a239bca
Source dataset
uspto-grants-1977_02
Patent number
US04008257

Reaction notes

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