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

HRID 878798Notes

Reaction equation

HRID 878798 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.[Si:26](Cl)([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27].O>ClCCl>[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)[Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 5870EstroneHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 118111023-O-(tert-Butyldimethylsilyl) EstroneYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of estrone (100 g, 0.37 mole) in 400 ml of dichloromethane, imidazole (50.36 g, 0.74 mole) and t-butyl-dimethylsilyl chloride (61.3 g, 0.41 mole) were added. The solution was stirred at room temperature for 24 hours. Then water (200 ml) was added. The organic layer was partially evaporated and diisopropyl ether added. The white solid formed was collected by filtration and dried. It weighed 135.2 g, yield 95%, mp 172° C.

Workup

  1. customThe organic layer was partially evaporated
  2. additiondiisopropyl ether added
  3. customThe white solid formed
  4. filtrationwas collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-f1e1a0adb26f4531bd6600ed6bd1ff28
Source dataset
uspto-grants-2015_03
Patent number
US08987484B2

Reaction notes

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