(5R)-2-iodo-5-(6-quinolyl)-5-(triethylsilyloxy)-2-pentene → (5R)-2-iodo-5-(6-quinolyl)-5-hydroxy-2-pentene

HRID 348252Notes

Reaction equation

HRID 348252 reaction equation
[I:1][C:2](=[CH:4][CH2:5][C@H:6]([C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[N:21]=[CH:20][CH:19]=[CH:18]2)[O:7][Si](CC)(CC)CC)[CH3:3]>C(O)(=O)C.C1COCC1.O>[I:1][C:2](=[CH:4][CH2:5][C@H:6]([C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[N:21]=[CH:20][CH:19]=[CH:18]2)[OH:7])[CH3:3]

Participants

3

Reactant 1

HCID 86586614(5R)-2-iodo-5-(6-quinolyl)-5-(triethylsilyloxy)-2-pentene

Product 1

HCID 86586613(5R)-2-iodo-5-(6-quinolyl)-5-hydroxy-2-pentene

Reagents, catalysts & solvents 1

HCID 21877175AcOH THF waterSolvent

Procedure

A solution of (5R)-2-iodo-5-(6-quinolyl)-5-(triethylsilyloxy)-2-pentene (2.26 g) in 50 mL of 3:1:1 acetic acid/THF/water is stirred at ambient temperature for 8 hours, then concentrated. The residue is dissolved in ethyl acetate, washed sequentially with sat. NaHCO3 and brine, then dried over MgSO4, filtered, and evaporated. The product is purified by SiO2 chromatography.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue is dissolved in ethyl acetate
  3. washwashed sequentially with sat. NaHCO3 and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe product is purified by SiO2 chromatography

Sources & evidence

ORD record
ord-b35dda08818246e48e57cbad89818865
Source dataset
uspto-grants-2007_02
Patent number
US07176235B2

Reaction notes

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