Sesamol → Ethyl 2-fluoro-6-[3,4-(methylenedioxy)phenoxy]benzoate

HRID 1600860Notes

Reaction equation

HRID 1600860 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:11]([F:12])=[CH:10][CH:9]=[CH:8][C:7]=1F)=[O:5])[CH3:2].[CH2:14]1[O:18][C:17]2[CH:19]=[C:20]([OH:23])[CH:21]=[CH:22][C:16]=2[O:15]1>CS(C)=O>[CH2:1]([O:3][C:4]([C:6]1[C:7]([O:23][C:20]2[CH:21]=[CH:22][C:16]3[O:15][CH2:14][O:18][C:17]=3[CH:19]=2)=[CH:8][CH:9]=[CH:10][C:11]=1[F:12])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 68289SesamolHCID 519631Ethyl 2,6-difluorobenzoate

Product 1

HCID 15540783Ethyl 2-fluoro-6-[3,4-(methylenedioxy)phenoxy]benzoateYield 61%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
80 °C

Procedure

A solution of ethyl-2,6-difluorobenzene-carboxylate (EXAMPLE 1C; 373 mg, 2.0 mmol) in DMSO (0.5 ml) was added to a solution of the solid prepared above in DMSO (1.0 ml). The brownish solution was heated at 80° C. for 2 hours. The solvent was evaporated, the solid filtered, washed with water several times and dried. The crude product was purified by flash column chromatography on silica gel using 3-15% ethyl acetate in hexane to give 371 mg of the product (61% yield) as a light yellow oil and unreacted sesamol.

Workup

  1. customThe solvent was evaporated
  2. filtrationthe solid filtered
  3. washwashed with water several times
  4. customdried
  5. customThe crude product was purified by flash column chromatography on silica gel using 3-15% ethyl acetate in hexane

Sources & evidence

ORD record
ord-bf02ab72fa914a93af81dca5886656c8
Source dataset
uspto-grants-1999_11
Patent number
US05977117

Reaction notes

Loading…