Acetone → HCID 22009848, compound

HRID 322250Notes

Reaction equation

HRID 322250 reaction equation
CS(OCCC[C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH2:18][C:19]2[N:20]=[C:21](/[CH:24]=[CH:25]/[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[O:22][CH:23]=2)[CH:10]=1)(=O)=O.[I-:32].[Na+].[CH3:34][C:35]([CH3:37])=O>O>[I:32][CH2:34][CH2:35][CH2:37][C:13]1[C:12]([O:15][CH3:16])=[C:11]([CH:10]=[CH:9][CH:14]=1)[O:17][CH2:18][C:19]1[N:20]=[C:21](/[CH:24]=[CH:25]/[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[O:22][CH:23]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 5238Sodium IodideHCID 22009736HCID 22009736, compound

Product 1

HCID 22009848HCID 22009848, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-[4-methoxy-3-[2-[(E)-2-phenylethenyl]-4-oxazolylmethoxy]phenyl]propyl methanesulfonate (900 mg), sodium iodide (3.00 g) and acetone (20 ml) was heated for one hour under reflux. The reaction mixture was poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4), and concentrated under reduced pressure. The residue was subjected to a silica gel column chromatography. From the fraction eluted with ethyl acetate-hexane (1:4, v/v), 4-[3-(3-iodopropyl)-2-methoxyphenoxymethyl]-2-[(E)-2-phenylethenyl]oxazole (905 mg, 95%) was obtained. Recrystallization from ethyl acetate-hexane gave colorless needles, mp 103-104° C.

Workup

  1. temperaturewas heated for one hour
  2. temperatureunder reflux
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with water
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under reduced pressure
  7. washFrom the fraction eluted with ethyl acetate-hexane (1:4, v/v)

Sources & evidence

ORD record
ord-50a8ffc0f91f4ea5a4def52c6aed91cb
Source dataset
uspto-grants-2001_04
Patent number
US06211215B1

Reaction notes

Loading…