Sodium Iodide → (S)-1-iodo-3-phenyl-3-propanol

HRID 247814

Reaction equation

HRID 247814 reaction equation
Cl[CH2:2][CH2:3][C@@H:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[OH:5].[I-:12].[Na+]>C(N(CC)CC)C.C(C(C)=O)C>[I:12][CH2:2][CH2:3][C@@H:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[OH:5]

Participants

5

Reactant 2

HCID 5238Sodium IodideHCID 2777894(S)-(-)-3-Chloro-1-phenyl-1-propanol

Product 1

HCID 14476876(S)-1-iodo-3-phenyl-3-propanolYield 74.9%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 6569Methyl Ethyl KetoneSolvent

Procedure

Commerically available (S)-3-chloro-1-phenyl-1-propanol (6 g) was heated with excess sodium iodide (4 equiv., 18 g) and a few drops of triethylamine in 30 mL of methyl ethyl ketone at 100° C. for 20 hours. A sample was taken and monitored by NMR to determine the extent of conversion. The solvent was removed in vacuo and the residue was taken up in dichloromethane and filtered to remove the salts and the iodoalcohol was purified by flash chromatography to yield 6.9 g of product.

Workup

  1. customThe solvent was removed in vacuo
  2. filtrationfiltered
  3. customto remove the salts
  4. customthe iodoalcohol was purified by flash chromatography

Sources & evidence

ORD record
ord-278df93dbd6b44d1b998b0215d6a2550
Source dataset
uspto-grants-1993_05
Patent number
US05208222

Linked notes

Loading…