HCID 89740138, compound → HCID 89740004, compound

HRID 1521803Notes

Reaction equation

HRID 1521803 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:15](=[CH:16][CH:17]=1)[C:8]1[S:9][C:10]([C:12](=[O:14])[CH3:13])=[CH:11][C:7]=1[CH2:6][CH2:5]2>C1(C)C=CC=CC=1.[O-2].[O-2].[Mn+4]>[Br:1][C:2]1[CH:3]=[C:4]2[C:15](=[CH:16][CH:17]=1)[C:8]1[S:9][C:10]([C:12](=[O:14])[CH3:13])=[CH:11][C:7]=1[CH:6]=[CH:5]2

Participants

4

Reactant 1

HCID 89740138HCID 89740138, compound

Product 1

HCID 89740004HCID 89740004, compoundYield 85.7%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

1-(7-bromo-4,5-dihydronaphtho[1,2-b]thiophen-2-yl) ethanone (11b) (600 mg, 1.95 mmol) was dissolved in 20 ml toluene and manganese dioxide (943 mg, 9.77 mmol) was added and the mixture was heated at 100° C. for 26 hr. Aliquots were taken in between to check the progress of the reaction by HPLC. Once the reaction was complete, the mixture was filtered over a pad of celite, and the celite pad was washed with ethyl acetate. The ethyl acetate layer was concentrated to obtain the desired compound (11c) (0.51 g, 85%). m/z 304, 306 (M+H)+.

Workup

  1. customthe progress of the reaction by HPLC
  2. filtrationthe mixture was filtered over a pad of celite
  3. washthe celite pad was washed with ethyl acetate
  4. concentrationThe ethyl acetate layer was concentrated

Sources & evidence

ORD record
ord-5c1084001a9540fa951915e7ea9877df
Source dataset
uspto-grants-2015_07
Patent number
US09073942B2

Reaction notes

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