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

HRID 343310

Reaction equation

HRID 343310 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.N1C=CN=C1.[C:26]([Si:30]([CH3:33])([CH3:32])Cl)([CH3:29])([CH3:28])[CH3:27]>CN(C=O)C>[Si:30]([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:26]([CH3:29])([CH3:28])[CH3:27])([CH3:33])[CH3:32]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 5870EstroneHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 118111023-O-(tert-Butyldimethylsilyl) EstroneYield 99%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of estrone (18, 8.10 g, 30.0 mmol) in DMF (25 mL) were added imidazole (3.07 g, 45 mmol) and tert-butyldimethylchlorosilane (5.42 g, 36 mmol) at room temperature. The reaction mixture was stirred for 18 h and then quenched with H2O (100 mL). The precipitate was collected by filtration and washed with H2O to afford 11.4 g of 50 (99% yield), m.p. 171°-172° C.

Workup

  1. customquenched with H2O (100 mL)
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with H2O

Sources & evidence

ORD record
ord-3f8593af807749a7b952fd47ee8a0488
Source dataset
uspto-grants-1999_01
Patent number
US05861388

Linked notes

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