Sodium Iodide → HCID 86592584, compound

HRID 1794985Notes

Reaction equation

HRID 1794985 reaction equation
Cl[CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1.[CH3:12][Si:13]([CH3:18])([CH3:17])[CH2:14][CH2:15][OH:16].C(N(CC)CC)C.[I-:26].[Na+]>ClCCl.CC(C)=O>[CH3:12][Si:13]([CH3:18])([CH3:17])[CH2:14][CH2:15][O:16][C:7](=[O:8])[C:6]1[CH:10]=[CH:11][C:3]([CH2:2][I:26])=[CH:4][CH:5]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 180132-(Trimethylsilyl)ethanolHCID 701364-(Chloromethyl)benzoyl chloride

Product 1

HCID 86592584HCID 86592584, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(chloromethyl)benzoyl chloride (2.5 g, 13.22 mmol) in dichloromethane (100 ml) was added 2-(trimethylsilyl)ethanol (1.72 ml, 12.0 mmol). Triethylamine (9.21 ml, 66 mmol) was added and the reaction mixture stirred overnight. The dichloromethane was evaporated and the crude material taken up in ether and washed with water. The ether layer was dried (sodium sulfate) and evaporated to give a slightly yellow mobile oil. The oil (2.7 g) was dissolved in acetone (30 ml) containing sodium iodide (1.5 g) and stirred for two hours. The solvent was removed, ether added and the reaction filtered. The filtrate was then evaporated to give the title compound as a brown temperature unstable oil, 3.58 g, 75%.

Workup

  1. customThe dichloromethane was evaporated
  2. washwashed with water
  3. dry with materialThe ether layer was dried (sodium sulfate)
  4. customevaporated
  5. customto give a slightly yellow mobile oil
  6. stirringstirred for two hours
  7. customThe solvent was removed
  8. additionether added
  9. filtrationthe reaction filtered
  10. customThe filtrate was then evaporated

Sources & evidence

ORD record
ord-c8c1ce6d8375423b890c12e818075b8e
Source dataset
uspto-grants-2006_04
Patent number
US07026304B2

Reaction notes

Loading…