Potassium Hydroxide → 6-(tert-butyl)-2-methyl-8H-indeno[2,1-b]thiophene

HRID 1868544Notes

Reaction equation

HRID 1868544 reaction equation
[C:1]([C:5]1[CH:16]=[CH:15][C:14]2[C:13]3[CH:12]=[C:11]([CH3:17])[S:10][C:9]=3[C:8](=O)[C:7]=2[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].O.NN.[OH-].[K+]>C(O)COCCO.O>[C:1]([C:5]1[CH:16]=[CH:15][C:14]2[C:13]3[CH:12]=[C:11]([CH3:17])[S:10][C:9]=3[CH2:8][C:7]=2[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 118177176-(tert-butyl)-2-methyl-8H-indeno[2,1-b]thiophen-8-one

Product 1

HCID 112650106-(tert-butyl)-2-methyl-8H-indeno[2,1-b]thiophene

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8117Diethylene GlycolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2.40 g (0.0095 mol) of 6-(tert-butyl)-2-methyl-8H-indeno[2,1-b]thiophen-8-one and 2.6 mL (0.05 mol) of hydrazine monohydrate in 25 mL of diethylene glycol was stirred at 80° C. in 40 min and then refluxed for 1 h. The resulting mixture was cooled to r.t., treated with a solution of 2.68 g (0.035 mol) of KOH in 9.4 mL of water and subsequently refluxed for 2 h. The resulting mixture was poured in 150 mL of water, the precipitate was filtered, washed 5 times with 100 mL of water and dried. Yield 1.25 g (54%).

Workup

  1. temperaturerefluxed for 1 h
  2. temperatureThe resulting mixture was cooled to r.t.
  3. temperaturesubsequently refluxed for 2 h
  4. filtrationthe precipitate was filtered
  5. washwashed 5 times with 100 mL of water
  6. customdried

Sources & evidence

ORD record
ord-5da0cede284a4219b81aebaed58f0af9
Source dataset
uspto-grants-2009_12
Patent number
US07635781B2

Reaction notes

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