Toluene → HCID 19360032, compound

HRID 1601127Notes

Reaction equation

HRID 1601127 reaction equation
[OH:1][C:2]1[O:6][N:5]([CH3:7])[C:4](=[O:8])[C:3]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[CH:17]=1.[C:24]1(C)C=CC=CC=1.C[Si](C=[N+]=[N-])(C)C>CO.CCCCCC>[CH3:24][O:1][C:2]1[O:6][N:5]([CH3:7])[C:4](=[O:8])[C:3]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[CH:17]=1

Participants

6

Reactant 3

HCID 1140TolueneHCID 167693TrimethylsilyldiazomethaneHCID 19360030HCID 19360030, compound

Product 1

HCID 19360032HCID 19360032, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8058HexaneSolvent

Procedure

5-Hydroxy-4-[2-(3-methoxyphenoxy)phenyl]-2-methyl-3(2H)-isoxazolone (2.5 g) was dissolved in 3 mL of methanol and 15 mL of toluene and cooled in an icebath. Trimethylsilyldiazomethane (5 mL of a 2.0 M solution in hexane) was added dropwise. Gas evolution was observed. The resulting yellow solution was stirred at room temperature overnight. The solvents were removed under reduced pressure and the residue was purified by flash chromatography (1:1 hexane:ethyl acetate as eluant). The second eluting component was collected to yield 950 mg (36%) of the title compound of Step D. 1H NMR (CDCl3): δ 7.51 (dd,J=1.7, 7.5 Hz, 1H), 7.27 (dt,J=1.7, 7.5 Hz, 1H), 7.17 (m,2H), 6.97 (dd,J=1, 8 Hz, 1H), 6.5 (m,3H), 3.92 (s,3H), 3.74 (s,3H), 3.33 (s,3H).

Workup

  1. customThe solvents were removed under reduced pressure
  2. customthe residue was purified by flash chromatography (1:1 hexane:ethyl acetate as eluant)
  3. customThe second eluting component was collected

Sources & evidence

ORD record
ord-0d74c0dc7d1145cbb30dabfdf3b46d42
Source dataset
uspto-grants-1999_11
Patent number
US05977149

Reaction notes

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