Sodium Iodide → HCID 14349148, compound

HRID 414831Notes

Reaction equation

HRID 414831 reaction equation
Cl[CH2:2][C:3]1[NH:4][CH:5]=[CH:6][CH:7]=1.[OH:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([OH:21])[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:11][CH:10]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CC(C)=O>[OH:21][CH:15]([C:12]1[CH:11]=[CH:10][C:9]([O:8][CH2:2][C:3]2[NH:4][CH:5]=[CH:6][CH:7]=2)=[CH:14][CH:13]=1)[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 10878034HCID 10878034, compoundHCID 21945725HCID 21945725, compound

Product 1

HCID 14349148HCID 14349148, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2-chloromethyl pyrrole (5.8 g, 0.05 mol), 1-(4-hydroxyphenyl)-1-hexanol (9.75 g, 0.05 mol), finely powdered anhydrous potassium carbonate (7 g, 0.05 mol) and sodium iodide (0.75 g, 0.005 mol) in anhydrous acetone (125 ml) were refluxed for 6 hours. The reaction mixture was filtered, and the residue was washed with acetone (25 ml). The filtrate was concentrated at the rotary evaporator to about 25-30 ml and the dark liquid was taken up in ethyl acetate (100 ml). The organic extract was washed with 5% sodium hydroxide solution, water and brine, and then dried over MgSO4. All volatiles were removed, and the dark oil was chromatographed on silica gel (15% ethyl acetate in hexanes) to leave the desired product as a light yellow liquid (4.1 g, 30%).

Workup

  1. temperaturewere refluxed for 6 hours
  2. filtrationThe reaction mixture was filtered
  3. washthe residue was washed with acetone (25 ml)
  4. concentrationThe filtrate was concentrated at the rotary evaporator to about 25-30 ml
  5. extractionThe organic extract
  6. washwas washed with 5% sodium hydroxide solution, water and brine
  7. dry with materialdried over MgSO4
  8. customAll volatiles were removed
  9. customthe dark oil was chromatographed on silica gel (15% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-f9b67fa19903466bab702b08664e6ca6
Source dataset
uspto-grants-1988_12
Patent number
US04794188

Reaction notes

Loading…