Methanol → HCID 19360028, compound

HRID 1289063Notes

Reaction equation

HRID 1289063 reaction equation
[OH:1][C:2]1[O:6]N[C:4](=[O:7])[C:3]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH3:22].[CH3:23]O.C[Si]([CH:29]=[N+:30]=[N-])(C)C>C1(C)C=CC=CC=1.O>[CH3:23][O:6][C:2]1[O:1][N:30]([CH3:29])[C:4](=[O:7])[C:3]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH3:22]

Participants

6

Reactant 3

HCID 887MethanolHCID 167693TrimethylsilyldiazomethaneHCID 193600335-Hydroxy-4-{2-[(2-methylphenoxy)methyl]phenyl}-1,2-oxazol-3(2H)-one

Product 1

HCID 19360028HCID 19360028, compoundYield 13%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
25 °C

Procedure

5-Hydroxy-4-[2-[(2-methylphenoxy)methyl]phenyl]-3(2H)-isoxazolone (31.3 g) was dissolved in 330 mL of 10:1 toluene:methanol and cooled in an ice-water bath. Trimethylsilyl-diazomethane (~2M in hexane) (55 mL) was added dropwise. Gas evolution was observed. The yellow solution was stirred at 25° C. for 2 h. The solution was diluted with 100 mL of water and extracted with ethyl acetate (4×100 mL). The combined organic extracts were dried (Mg SO4), filtered and concentrated under reduced pressure to yield an oil, which was purified by flash chromatography (silica gel; 1:1 hexane:ethyl acetate as eluant). The second eluting component was collected to yield 4.35 g (13%) of the title compound of Step E as a white solid, mp 90°-92° C. 1H NMR (CDCl3) δ7.61(d,1H), 7.35(m,3H), 7.12(m,2H), 6.84(m,2H), 5.12(s,2H), 3.96(s,3H), 3.41(s,3H), 2.24(s, 3H).

Workup

  1. extractionextracted with ethyl acetate (4×100 mL)
  2. dry with materialThe combined organic extracts were dried (Mg SO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customto yield an oil, which
  6. customwas purified by flash chromatography (silica gel; 1:1 hexane:ethyl acetate as eluant)
  7. customThe second eluting component was collected

Sources & evidence

ORD record
ord-28bf8fc52f5e4b61a6ce697d1e72a691
Source dataset
uspto-grants-1998_05
Patent number
US05747516

Reaction notes

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