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

HRID 1357414Notes

Reaction equation

HRID 1357414 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-d0132a35104940bda294966c848d7896
Source dataset
uspto-grants-2003_07
Patent number
US06589968B2

Reaction notes

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