Pyridine → 7-furyl-3-methyl-4-chromanone O-(toluenesulfonyl)-oxime

HRID 49438Notes

Reaction equation

HRID 49438 reaction equation
[C:1]1([CH3:11])[C:2]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1.[O:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[C:17]1[CH:26]=[C:25]2[C:20]([C:21](=[N:28][OH:29])[CH:22]([CH3:27])[CH2:23][O:24]2)=[CH:19][CH:18]=1.N1C=CC=CC=1>C(Cl)Cl>[C:1]1([CH3:11])[C:2]([S:7]([O:29][N:28]=[C:21]2[C:20]3[C:25](=[CH:26][C:17]([C:13]4[O:12][CH:16]=[CH:15][CH:14]=4)=[CH:18][CH:19]=3)[O:24][CH2:23][CH:22]2[CH3:27])(=[O:9])=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 8623o-Toluenesulfonyl chlorideHCID 73868111HCID 73868111, compound

Product 1

HCID 865864777-furyl-3-methyl-4-chromanone O-(toluenesulfonyl)-oximeYield 57.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Toluenesulfonyl chloride (397 mg, 2.08 mmol) was added to a 0° C. solution of 7-furyl-3-methyl-4-chromanone oxime (61) (461 mg, 1.89 mmol) and pyridine (0.5 mL) in CH2Cl2 (10 mL). After 6 hours, the mixture was diluted with CH2Cl2 (30 mL) and washed with 5% HCl (20 mL). The organic layer was dried over MgSO4, filtered and concentrated. The residue was purified via flash chromatography using 5:1 hexanes:EtOAc as the eluent, to provide 7-furyl-3-methyl-4-chromanone O-(toluenesulfonyl)-oxime (62) (429 mg) as a pink solid, m.p. 163-164° C. (dec).

Workup

  1. washwashed with 5% HCl (20 mL)
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified via flash chromatography

Sources & evidence

ORD record
ord-e2efc53ca1894beeb3afa35c33fbafd0
Source dataset
uspto-grants-2004_03
Patent number
US06706740B2

Reaction notes

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