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

HRID 2181758Notes

Reaction equation

HRID 2181758 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-4e44a5989e56459daf029e30de3d9263
Source dataset
uspto-grants-2005_05
Patent number
US06893859B2

Reaction notes

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