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

HRID 1003176Notes

Reaction equation

HRID 1003176 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 (11, 8.10 g, 30.0 mmol) in DMF (25 mL) were added imidazole (3.07 g, 45 mmol) and tert-butyldimethyl-chlorosilane (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 29 (99% yield) mp: 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-07e85c9db4c64443b8d1d4605be2b297
Source dataset
uspto-grants-2000_04
Patent number
US06046186

Reaction notes

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