Sodium Iodide → (S)-methyl 2-(tert-butyldimethylsilyloxy)-4-iodobutanoate

HRID 656616Notes

Reaction equation

HRID 656616 reaction equation
[Si:1]([O:8][C@@H:9]([CH2:14][CH2:15]S(C)(=O)=O)[C:10]([O:12][CH3:13])=[O:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[I-:20].[Na+]>CC(C)=O>[Si:1]([O:8][C@@H:9]([CH2:14][CH2:15][I:20])[C:10]([O:12][CH3:13])=[O:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 86636767(S)-methyl 2-(tert-butyldimethylsilyloxy)-4-mesylbutanoate

Product 1

HCID 57999041(S)-methyl 2-(tert-butyldimethylsilyloxy)-4-iodobutanoateYield 80%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of (S)-methyl 2-(tert-butyldimethylsilyloxy)-4-mesylbutanoate (91d, 4.9 g, 15 mmol) in anhydrous acetone was added sodium iodide (11.5 g, 75 mmol). The reaction was heated at reflux for 1.5 h. The reaction was quenched with water and extracted into EtOAc×3. The combined organic phases were washed with brine then dried over anhydrous sodium sulfate. The solvent was removed in vacuo to yield (S)-methyl 2-(tert-butyldimethylsilyloxy)-4-iodobutanoate (91e, 4.33 g, 12 mmol) as a yellow oil. 1H NMR (400 MHz, CHLOROFORM-d) δ 0.07-0.13 (m, 6H), 0.82-0.99 (m, 9H), 2.09-2.32 (m, 2H), 3.17-3.36 (m, 2H), 3.74 (s, 3H), 4.29 (dd, J=8.08, 4.04 Hz, 1H).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 1.5 h
  3. customThe reaction was quenched with water
  4. extractionextracted into EtOAc×3
  5. washThe combined organic phases were washed with brine
  6. dry with materialthen dried over anhydrous sodium sulfate
  7. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-81b0f33bb27641008d4af138335c47f7
Source dataset
uspto-grants-2011_12
Patent number
US08071766B2

Reaction notes

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