Imidazole → 3-O-(tert-Butyldimethylsilyl) Estrone

HRID 1005305Notes

Reaction equation

HRID 1005305 reaction equation
[CH3:1][C@@:2]12[C:18](=[O:19])[CH2:17][CH2:16][C@H:15]1[C@H:14]1[C@@H:5]([C:6]3[CH:7]=[CH:8][C:9]([OH:20])=[CH:10][C:11]=3[CH2:12][CH2:13]1)[CH2:4][CH2:3]2.[Si:21](Cl)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22].N1C=CN=C1>C1COCC1.CN(C=O)C>[Si:21]([O:20][C:9]1[CH:8]=[CH:7][C:6]2[C@@H:5]3[C@H:14]([C@H:15]4[C@@:2]([CH2:3][CH2:4]3)([CH3:1])[C:18](=[O:19])[CH2:17][CH2:16]4)[CH2:13][CH2:12][C:11]=2[CH:10]=1)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 5870EstroneHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 118111023-O-(tert-Butyldimethylsilyl) EstroneYield 94%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of estrone (1, 29 g, 107.3 mmol) and tert-butyldimethylsilyl chloride (18 g, 118 mmol) in THF (350 mL) at room temperature under argon was added imidazole (18 g, 264 mmol) in DMF (350 mL). After stirring the reaction mixture overnight, the THF was evaporated and the reaction mixture was poured onto ice water. The resulting white precipitate was collected by filtration, dissolved in CH2Cl2, and the solution was dried (MgSO4). The desiccant was filtered and the solvent was evaporated under reduced pressure to afford 38.8 g of 2 as a white, crystalline solid (94% yield), m.p. 171-172° C.

Workup

  1. customthe THF was evaporated
  2. additionthe reaction mixture was poured onto ice water
  3. filtrationThe resulting white precipitate was collected by filtration
  4. dissolutiondissolved in CH2Cl2
  5. dry with materialthe solution was dried (MgSO4)
  6. filtrationThe desiccant was filtered
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-d041a9bf12604175aa06ffada713972f
Source dataset
uspto-grants-2000_04
Patent number
US06054446

Reaction notes

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