Potassium Carbonate → 3-(3-Epoxymethoxyphenyl)thieno[2,3-d]isoxazole

HRID 622225Notes

Reaction equation

HRID 622225 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8]2[C:12]3[S:13][CH:14]=[CH:15][C:11]=3[O:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.C(C1[O:20][CH2:19]1)Br.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(#N)C>[O:1]1[C:7]2[CH:6]=[CH:5][C:4]([C:8]3[C:12]4[S:13][CH:14]=[CH:15][C:11]=4[O:10][N:9]=3)=[C:3]([O:20][CH3:19])[C:2]1=2

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 18430EpibromohydrinHCID 140972423-Thieno[2,3-d]isoxazol-3-yl-phenol

Product 1

HCID 867420163-(3-Epoxymethoxyphenyl)thieno[2,3-d]isoxazoleYield 73.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 28 g of 3-(3-hydroxyphenyl)thieno[2,3-d]isoxazole, 23 g of epibromohydrin and 30 g of milled potassium carbonate in 40 ml of dimethylformamide and 40 ml of acetonitrile was stirred under nitrogen at 90°-100° C. until completion of reaction. The reaction was complete after 4 hours and allowed to cool to room temperature. Quenching with water (400 ml), extracting with 50/50 ether/ethyl acetate soluiton (3×400 ml), and washing with water (2×400 ml) were conducted. The organics were dried over anhydrous magnesium sulfate and the solvents were evaporated to give an oil. The oil was purified by HPLC (4:1 hexane/ethyl acetate) to yield 23.3 g of a solid with a melting point of 88°-90° C.

Workup

  1. customQuenching with water (400 ml)
  2. extractionextracting with 50/50 ether/ethyl acetate soluiton (3×400 ml)
  3. washwashing with water (2×400 ml)
  4. dry with materialThe organics were dried over anhydrous magnesium sulfate
  5. customthe solvents were evaporated
  6. customto give an oil
  7. customThe oil was purified by HPLC (4:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-388054d474674c9f90e80ccf0f1caf35
Source dataset
uspto-grants-1988_09
Patent number
US04769472

Reaction notes

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