Water → 3-(2-Fluorophenyl)-6-methoxy-7-methyl-1,2-benzisoxazole

HRID 652886Notes

Reaction equation

HRID 652886 reaction equation
C(O/[N:5]=[C:6](/[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[F:23])\[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]([CH3:15])[C:8]=1[OH:16])(=O)C.[H-].[Na+].O>CN(C=O)C>[F:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[C:6]1[C:7]2[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]([CH3:15])[C:8]=2[O:16][N:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 136477425[(E)-[(2-fluorophenyl)-(2-hydroxy-4-methoxy-3-methylphenyl)methylidene]amino] acetate

Product 1

HCID 130157283-(2-Fluorophenyl)-6-methoxy-7-methyl-1,2-benzisoxazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

E-2'-fluoro-2-hydroxy-4-methoxy-3-methylbenzophenone O-acetyl oxime (22.0 g) is dissolved in 100 ml of DMF and added to a suspension of 2.5 g NaH in 100 ml DMF. An ice bath is applied to keep the reaction temperature <30° C. After 40 minutes the reaction is poured into H2O and extracted with ether. After washing well with H2O, the ether is dried and evaporated to give a crystalline product that is washed with cold hexane to give 3-(2-fluorophenyl)-6-methoxy-7-methyl-1,2-benzisoxazole, mp 105°-108° C.

Workup

  1. customAn ice bath is applied
  2. customthe reaction temperature <30° C
  3. extractionextracted with ether
  4. washAfter washing well with H2O
  5. dry with materialthe ether is dried
  6. customevaporated
  7. customto give a crystalline product that
  8. washis washed with cold hexane

Sources & evidence

ORD record
ord-c880560544e348d9a6612b3c03c05afd
Source dataset
uspto-grants-1987_06
Patent number
US04673746

Reaction notes

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