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

HRID 878799Notes

Reaction equation

HRID 878799 reaction equation
[OH:1][C:2]1[CH:19]=[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:20])[CH2:10][CH2:9]4)[CH2:6][CH2:5][C:4]=2[CH:3]=1.[Si:21](Cl)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22].N1C=CN=C1.O>ClCCl>[Si:21]([O:1][C:2]1[CH:19]=[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:20])[CH2:10][CH2:9]4)[CH2:6][CH2:5][C:4]=2[CH:3]=1)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22]

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 3-hydroxy-estra-1,3,5(10)-triene-17-one (100 g, 0.370 mole) in 500 ml of dichloromethane was added tert-butyldimethylsilyl-chloride (58.3 g, 0.388 mole) and imidazole (26.4 g, 0.388 mole). The mixture was stirred for 24 hours at room temperature. Water (300 ml) was added and the organic layer was washed with 200 ml of water. After concentration the product was crystallized from a mixture of ethanol/diisopropyl ether, collected by filtration and dried. It weighed 145 g (95% yield).

Workup

  1. washthe organic layer was washed with 200 ml of water
  2. concentrationAfter concentration the product
  3. customwas crystallized from a mixture of ethanol/diisopropyl ether
  4. filtrationcollected by filtration
  5. customdried

Sources & evidence

ORD record
ord-373de7c6b8564bb58c8a4cec6730224d
Source dataset
uspto-grants-2015_03
Patent number
US08987484B2

Reaction notes

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