Isopropyl iodide → HCID 11101724, compound

HRID 1584351Notes

Reaction equation

HRID 1584351 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]([CH3:27])=[C:9]([CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][CH2:21][C:22]([OH:24])=[O:23])=[CH:15][C:14]=2[O:25][CH3:26])[N:10]=1.[CH:28](I)([CH3:30])[CH3:29].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]([CH3:27])=[C:9]([CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][CH2:21][C:22]([O:24][CH:28]([CH3:30])[CH3:29])=[O:23])=[CH:15][C:14]=2[O:25][CH3:26])[N:10]=1

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 11728394HCID 11728394, compound

Product 1

HCID 11101724HCID 11101724, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-[4-[2-(2-furyl)-5-methyl-4-oxazolyl methoxy]-3-methoxyphenyl]butanoic acid (106 g), isopropyl iodide (58.2 g), potassium carbonate (47.3 g) and N,N-dimethylformamide (DMF) (100 ml) was stirred for 4 hours at temperatures ranging from 65 to 70° C. The reaction mixture was poured into ice-water, which was subjected to extraction with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4) and then concentrated. The concentrate was subjected to column chromatography on silica gel. From the fraction eluted with ethyl acetate-hexane (1:2), was obtained isopropyl 4-[4-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]-3-methoxyphenyl]butanoate (107 g, 91%), which was recrystallized from acetone-hexane to give colorless needles, m.p.45-46° C.

Workup

  1. customranging from 65 to 70° C
  2. extractionwas subjected to extraction with ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. washFrom the fraction eluted with ethyl acetate-hexane (1:2)

Sources & evidence

ORD record
ord-26ca0fd5105b47feba5a64bf30fc3709
Source dataset
uspto-grants-1999_08
Patent number
US05932601

Reaction notes

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