Benzene → HCID 44375475, compound

HRID 1816490Notes

Reaction equation

HRID 1816490 reaction equation
[Si]([O:8][C@H:9]1[CH2:33][CH2:32][C@@:31]2([CH3:34])[C:11](=[CH:12][CH:13]=[C:14]3[C@@H:30]2[CH2:29][CH2:28][C@@:27]2([CH3:35])[C@H:15]3[CH2:16][CH2:17][C@@H:18]2[C@H:19]([CH3:26])[CH2:20][CH2:21][CH2:22][C:23]([CH3:25])=[CH2:24])[C:10]1([CH3:37])[CH3:36])(C(C)(C)C)(C)C.C1C=CC=CC=1.[ClH:44]>C(O)C>[Cl:44][C:23]([CH2:22][CH2:21][CH2:20][C@H:19]([C@@H:18]1[C@:27]2([CH3:35])[C:15]([C:14]3[CH2:13][CH2:12][C@@H:11]4[C@:31]([C:30]=3[CH2:29][CH2:28]2)([CH3:34])[CH2:32][CH2:33][C@H:9]([OH:8])[C:10]4([CH3:37])[CH3:36])=[CH:16][CH2:17]1)[CH3:26])([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 241BenzeneHCID 313Hydrochloric AcidHCID 69411903HCID 69411903, compound

Product 1

HCID 44375475HCID 44375475, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3β-(tert-butyldimethylsilyloxy)-4,4-dimethylcholesta-5,7,25-triene (50 mg), benzene (5 mL), ethanol (5 mL) and concentrated HCl (2 mL) was heated under reflux for 4 hours. The reaction was concentrated to half volume under reduced pressure and water (5 mL) was added. Extraction of the aqueous phase with dichloromethane and concentration under reduced pressure gave a residue, which was purified by flash chromatography. Recrystallisation from ethyl acetate:hexane gave the title compound as a white solid (35 mg).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 hours
  3. concentrationThe reaction was concentrated to half volume under reduced pressure and water (5 mL)
  4. additionwas added
  5. extractionExtraction of the aqueous phase
  6. concentrationwith dichloromethane and concentration under reduced pressure
  7. customgave a residue, which
  8. customwas purified by flash chromatography
  9. customRecrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-422e06903cc64a21b32c52a308dd6b28
Source dataset
uspto-grants-2005_04
Patent number
US06884796B2

Reaction notes

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