(5R)-2-iodo-6-methyl-7-(2-methylthiazol-4-yl)-5-(triethylsilyloxy)-2,6-heptadiene → (5R)-5-hydroxy-2-iodo-6-methyl-7-(2-methylthiazol-4-yl)-2,6-heptadiene

HRID 1357412Notes

Reaction equation

HRID 1357412 reaction equation
[I:1][C:2](=[CH:4][CH2:5][C@@H:6]([O:16][Si](CC)(CC)CC)[C:7]([CH3:15])=[CH:8][C:9]1[N:10]=[C:11]([CH3:14])[S:12][CH:13]=1)[CH3:3]>C(O)(=O)C.C1COCC1.O>[OH:16][C@@H:6]([C:7]([CH3:15])=[CH:8][C:9]1[N:10]=[C:11]([CH3:14])[S:12][CH:13]=1)[CH2:5][CH:4]=[C:2]([I:1])[CH3:3]

Participants

3

Reactant 1

HCID 86586611(5R)-2-iodo-6-methyl-7-(2-methylthiazol-4-yl)-5-(triethylsilyloxy)-2,6-heptadiene

Product 1

HCID 86586610(5R)-5-hydroxy-2-iodo-6-methyl-7-(2-methylthiazol-4-yl)-2,6-heptadiene

Reagents, catalysts & solvents 1

HCID 21877175AcOH THF waterSolvent

Procedure

A solution of (5R)-2-iodo-6-methyl-7-(2-methylthiazol-4-yl)-5-(triethylsilyloxy)-2,6-heptadiene (2.28 g) in 50 mL of 3:1:1 acetic acid/THF/water is stirred at ambient temperature for 8 hoursours, 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 (30% ethyl acetate/hexanes).

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 (30% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-0e7fe13a50944992a70456975b83e0c6
Source dataset
uspto-grants-2003_07
Patent number
US06589968B2

Reaction notes

Loading…