Imidazole → HCID 18608961, compound

HRID 2118954Notes

Reaction equation

HRID 2118954 reaction equation
[CH3:1][C@:2]12[CH2:18][CH2:17][C@H:16]3[C@@H:7]([CH2:8][CH2:9][C:10]4[CH:11]=[C:12]([OH:19])[CH:13]=[CH:14][C:15]=43)[C@@H:6]1[CH2:5][C@@H:4]([OH:20])[C@@H:3]2[OH:21].N1C=CN=C1.[C:27]([Si:31](Cl)([CH3:33])[CH3:32])([CH3:30])([CH3:29])[CH3:28]>CN(C)C=O>[Si:31]([O:20][C@@H:4]1[CH2:5][C@H:6]2[C@H:7]3[C@H:16]([CH2:17][CH2:18][C@:2]2([CH3:1])[C@H:3]1[OH:21])[C:15]1[CH:14]=[CH:13][C:12]([OH:19])=[CH:11][C:10]=1[CH2:9][CH2:8]3)([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:33])[CH3:32]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 5756EstriolHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 18608961HCID 18608961, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 11.52 g of 1,3,5(10)-estratriene-3,16α,17β-triol in 200 ml of dimethylformamide, cooled to -20° C., is combined, after adding 6.52 g of imidazole, dropwise with a solution of 13.24 g of tertbutyldimethylsilyl chloride in 100 ml of dimethylformamide. This reaction mixture is stirred for one hour with continued cooling and then poured into ice water. The resultant precipitate is filtered off, washed with water and dissolved in dichloromethane. The solution is dried over sodium sulfate and evaporated under vacuum. The residue is chromatographed on silica gel.

Workup

  1. temperaturewith continued cooling
  2. filtrationThe resultant precipitate is filtered off
  3. washwashed with water
  4. dissolutiondissolved in dichloromethane
  5. dry with materialThe solution is dried over sodium sulfate
  6. customevaporated under vacuum
  7. customThe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-07ebdfd0bf0249f6ac862119adc1c275
Source dataset
uspto-grants-1987_07
Patent number
US04681875

Reaction notes

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