Sodium Iodide → HCID 22184410, compound

HRID 1794984Notes

Reaction equation

HRID 1794984 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6](Cl)=[O:7].[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:6](=[O:7])[C:5]1[CH:9]=[CH:10][CH:11]=[C:3]([CH2:2][I:26])[CH:4]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 180132-(Trimethylsilyl)ethanolHCID 27333243-(Chloromethyl)benzoyl chloride

Product 1

HCID 22184410HCID 22184410, compoundYield 101.5%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(chloromethyl)benzoyl chloride (2.5 g, 17.5 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 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 and to the residue was added diethyl ether and the resulting mixture was filtered. The filtrate was evaporated to give a brown oil (3.68 g, 77%): 1H NMR (CDCl3) δ: 7.95, (1H, s), 7.85, (1H, d), 7.28, (1H, d), 7.17, (1H, t), 4.38, (2H, s), 4.33 (2H, m), 1.11 (2H, m), 0.00 (9H, s) ppm. Mass spectrum (M-I) 235.

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 and to the residue
  8. additionwas added diethyl ether
  9. filtrationthe resulting mixture was filtered
  10. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-fd9a841639d6442b8ae00e56d45c0914
Source dataset
uspto-grants-2006_04
Patent number
US07026304B2

Reaction notes

Loading…