Hydrochloric Acid → HCID 20599275, compound

HRID 479318Notes

Reaction equation

HRID 479318 reaction equation
[CH3:1][C:2]1([CH3:38])[C:26](=[O:27])[CH2:25][CH2:24][C@@:23]2([CH3:28])[C:3]1=[CH:4][CH2:5][C@@H:6]1[C@@H:22]2[CH2:21][CH2:20][C@@:19]2([CH3:29])[C@H:7]1[CH2:8][C@H:9]([O:30][Si](C(C)(C)C)(C)C)[C@@H:10]2[C@H:11]([CH3:18])[CH2:12][CH2:13][CH2:14][CH:15]([CH3:17])[CH3:16].Cl>C(O)C>[CH3:38][C:2]1([CH3:1])[C:26](=[O:27])[CH2:25][CH2:24][C@@:23]2([CH3:28])[C:3]1=[CH:4][CH2:5][C@@H:6]1[C@@H:22]2[CH2:21][CH2:20][C@@:19]2([CH3:29])[C@H:7]1[CH2:8][CH:9]([OH:30])[C@@H:10]2[C@H:11]([CH3:18])[CH2:12][CH2:13][CH2:14][CH:15]([CH3:17])[CH3:16]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69886665HCID 69886665, compound

Product 1

HCID 20599275HCID 20599275, compoundYield 66.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4,4-dimethyl-16β-(tert-butyldimethylsilyloxy)cholest-5-en-3-one (40 mg, 0.07 mmol), concentrated HCl (0.2 mL) and ethanol (5 mL) were heated to reflux for 20 hours. Removal of solvent under reduced pressure and recrystallization twice from methanol gave 4,4-dimethylcholest-5-en-16-ol-3-one (20 mg).

Workup

  1. temperaturewere heated
  2. temperatureto reflux for 20 hours
  3. customRemoval of solvent
  4. customunder reduced pressure and recrystallization twice from methanol

Sources & evidence

ORD record
ord-a6bebadc88b44d29a4c60525eaabb932
Source dataset
uspto-grants-2003_11
Patent number
US06645953B2

Reaction notes

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