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Imidazole → HCID 10342619, compound

HRID 1003196
Notes
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Reaction equation

HRID 1003196 reaction equation
[OH:1][C:2]1[C:19]([N+:20]([O-:22])=[O:21])=[CH:18][C:17]2[C@@H:16]3[C@H:7]([C@H:8]4[C@@:12]([CH2:14][CH2:15]3)([CH3:13])[C:11](=[O:23])[CH2:10][CH2:9]4)[CH2:6][CH2:5][C:4]=2[CH:3]=1.N1C=CN=C1.[C:29]([Si:33]([CH3:36])([CH3:35])Cl)([CH3:32])([CH3:31])[CH3:30]>CN(C=O)C.CCOC(C)=O>[Si:33]([O:1][C:2]1[C:19]([N+:20]([O-:22])=[O:21])=[CH:18][C:17]2[C@@H:16]3[C@H:7]([C@H:8]4[C@@:12]([CH2:14][CH2:15]3)([CH3:13])[C:11](=[O:23])[CH2:10][CH2:9]4)[CH2:6][CH2:5][C:4]=2[CH:3]=1)([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:36])[CH3:35]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 2334963-Hydroxy-2-nitroestra-1,3,5(10)-trien-17-one

Product 1

HCID 10342619HCID 10342619, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent
HCID 8857
Ethyl Acetate
Solvent

Procedure

To a solution of 3-hydroxy-2-nitroestra-1,3,5(10)-trien-17-one (76b, 1.10 g, 3.5 mmol) in DMF (10 mL) were added imidazole (0.476 g, 7.0 mmol) and tert-butyldimethylchlorosilane (0.690 g, 4.6 mmol) at room temperature. The reaction mixture was stirred for 1 h, and diluted with EtOAc, and washed with H2O, saturated aqueous NaCl, and then dried (Na2SO4). The desiccant was filtered and the solvent was evaporated at reduced pressure. The residue was purified by column chromatography (silica gel) using n-hexane:EtOAc (5:1→2:1, v/v) to afford 1.45 g of 89 (97% yield) mp: 184-185° C.

Workup

  1. washwashed with H2O, saturated aqueous NaCl
  2. dry with materialdried (Na2SO4)
  3. filtrationThe desiccant was filtered
  4. customthe solvent was evaporated at reduced pressure
  5. customThe residue was purified by column chromatography (silica gel)

Sources & evidence

ORD record
ord-627d20e38b0a45e489458e34fff8b08d
Source dataset
uspto-grants-2000_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06046186

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes