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Imidazole → HCID 14800132, compound

HRID 2082255
Notes
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Reaction equation

HRID 2082255 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]2[C@H:8]3[C@H:17]([CH2:18][CH2:19][C@:3]12[CH3:4])[C@@H:16]1[C@H:11]([CH2:12][C:13](=[O:20])[CH2:14][CH2:15]1)[CH2:10][CH2:9]3.N1C=CN=C1.[C:26]([Si:30](Cl)([CH3:32])[CH3:31])([CH3:29])([CH3:28])[CH3:27].CCCCCC.CCOC(C)=O>CN(C=O)C.O>[Si:30]([O:1][C@H:2]1[CH2:7][CH2:6][C@H:5]2[C@H:8]3[C@H:17]([CH2:18][CH2:19][C@:3]12[CH3:4])[C@@H:16]1[C@H:11]([CH2:12][C:13](=[O:20])[CH2:14][CH2:15]1)[CH2:10][CH2:9]3)([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:32])[CH3:31]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 9420217beta-Hydroxy-5alpha-estran-3-oneHCID 21226206Ethyl acetate hexane

Product 1

HCID 14800132HCID 14800132, compoundYield 99.1%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

10 g of 17β-hydroxy-5α-estran-3-one was dissolved in 150 ml of DMF. 3.7 g of imidazole were then added and the mixture was cooled to 0° C. 6.5 g of t-butyl dimethyl silyl chloride were added and the mixture was stirred and gradually warmed to room temperature followed by stirring for two days. TLC (hexane/EtOAc (9:1)) revealed that the reaction was complete. The reaction mixture was diluted with water and then extracted with 500 ml of hexane/EtOAc (9:1) (2x). The combined organic layers were washed with brine, dried over MgSO4, filtered, and evaporated under reduced pressure to produce crude product (14.6 g). The entire crude yield was flash chromatographed with the Aldrich flash chromatography system. The 600 ml column was filled with 7 inches of 230-400 mesh silica gel, eluting with hexane/EtOAc (10:1). Once the sample was loaded, 30 ml fractions were taken. Fraction numbers 4-13, yielded 14 g of the title compound, m.p. 103°-104° C.

Workup

  1. temperaturegradually warmed to room temperature
  2. stirringby stirring for two days
  3. extractionextracted with 500 ml of hexane/EtOAc (9:1) (2x)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customto produce crude product (14.6 g)
  9. customThe entire crude yield
  10. customchromatographed with the Aldrich flash chromatography system
  11. additionThe 600 ml column was filled with 7 inches of 230-400 mesh silica gel
  12. washeluting with hexane/EtOAc (10:1)

Sources & evidence

ORD record
ord-04192a827a844c9c87f8cba29cc7c570
Source dataset
uspto-grants-1993_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05187299

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes