HCID 68725493, compound → HCID 21498017, compound

HRID 1892063Notes

Reaction equation

HRID 1892063 reaction equation
C(O[CH:4](OCC)[CH2:5][S:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][C:8]=1[CH3:15])C>ClC1C=CC=CC=1.O>[CH3:15][C:8]1[C:7]2[S:6][CH:5]=[CH:4][C:12]=2[CH:11]=[C:10]([O:13][CH3:14])[CH:9]=1

Participants

4

Reactant 1

HCID 68725493HCID 68725493, compound

Product 1

HCID 21498017HCID 21498017, compoundYield 44.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7964ChlorobenzeneSolvent2×

Procedure

To the hot (130° C.) solution of polyphosphoric acid (20 mL) in chlorobenzene (50 mL) was added dropwise a solution of 1-(2,2-diethoxy-ethylsulfanyl)-4-methoxy-2-methyl-benzene from step 2 (6.8 g, 0.025 mol) in chlorobenzene (25 mL) over a period of 2 h and stirred for 2 h at same temperature. The reaction mixture was cooled to room temperature and stirred for 12 h. The mixture was then cooled and diluted with water and the layers were separated. The aqueous layer was extracted in ethyl acetate. The combined organic layers were washed with water, dried and concentrated. The crude material was purified by chromatography (silica gel: hexane:ethyl acetate/4:1) to provide 2 g of 7-methyl-5-methoxy benzothiophene. MS m/z 178 (M+).

Workup

  1. stirringstirred for 12 h
  2. temperatureThe mixture was then cooled
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted in ethyl acetate
  5. washThe combined organic layers were washed with water
  6. customdried
  7. concentrationconcentrated
  8. customThe crude material was purified by chromatography (silica gel: hexane:ethyl acetate/4:1)

Sources & evidence

ORD record
ord-1703f3d026004071ad9431b6f96baa4c
Source dataset
uspto-grants-2013_08
Patent number
US08507509B2

Reaction notes

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