HCID 54553429, compound → HCID 53781446, compound

HRID 1073885Notes

Reaction equation

HRID 1073885 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH3:9])=[CH:4][C:3]=1[CH:10]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N+:16]=1[O-:21])[CH:11]=[C:12]([CH3:14])[CH3:13]>ClCCl.S(=O)(=O)(O)O>[CH3:13][C:12]1([CH3:14])[CH2:11][CH:10]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N+:16]=2[O-:21])[C:3]2[CH:4]=[C:5]([S:8][CH3:9])[CH:6]=[CH:7][C:2]=2[O:1]1

Participants

4

Reactant 1

HCID 54553429HCID 54553429, compound

Product 1

HCID 53781446HCID 53781446, compoundYield 93.6%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 6344DichloromethaneSolvent2×

Procedure

0.47 g of 2-[1-(2-hydroxy-5-methylthiophenyl)-3-methyl-2-butenyl]pyridine N-oxide was taken up in 10 ml of dichloromethane and stirred with 5 drops of sulphuric acid for 1 hour at 20° C. The mixture was diluted with 20 ml of dichloromethane and washed with aqueous sodium carbonate solution. The organic phase was evaporated and the residue was chromatographed on silica gel using diethyl ether/methanol (19:1) for the elution to give 0.44 g of 2-(3,4-dihydro-2,2-dimethyl-6methylthio-2H-1-benzopyran-4-yl)pyridine N-oxide in the form of a pale yellow oil.

Workup

  1. washwashed with aqueous sodium carbonate solution
  2. customThe organic phase was evaporated
  3. customthe residue was chromatographed on silica gel
  4. washfor the elution

Sources & evidence

ORD record
ord-12b6fc3b19834bbcb8eb7985490f199d
Source dataset
uspto-grants-1990_11
Patent number
US04971982

Reaction notes

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