Potassium Hydroxide → 2-Isobutylthiophene

HRID 252252Notes

Reaction equation

HRID 252252 reaction equation
[OH-].[K+].O.NN.[CH3:6][CH:7]([CH3:15])[C:8]([C:10]1[S:11][CH:12]=[CH:13][CH:14]=1)=O>C(O)COCCO.O>[CH2:8]([C:10]1[S:11][CH:12]=[CH:13][CH:14]=1)[CH:7]([CH3:15])[CH3:6]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 38624802-Methyl-1-(thiophen-2-yl)propan-1-one

Product 1

HCID 5664322-Isobutylthiophene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8117Diethylene GlycolSolvent

Conditions

Temperature
180 °C

Procedure

To a mixture of potassium hydroxide (2.24 g, 40 mmol) and hydrazine monohydrate (3.0 g, 60 mmol) in diethylene glycol (25 ml) was added 2-methyl-1-thiophen-2-yl-propan-1-one (1.54 g, 10 mmol). The combined mixture was heated at 180° C. for 1 h and then at 210° C. for a further 2 h. The mixture was cooled to rt and diluted with water (100 ml) and extracted with diethyl ether (3×). The combined organic extracts were washed with water, brine, dried (Na2SO4), filtered and concentrated under reduced pressure to yield a yellow oil: 0.9 g (61%) GC-MS: M=140.0.

Workup

  1. temperatureThe mixture was cooled to rt
  2. extractionextracted with diethyl ether (3×)
  3. washThe combined organic extracts were washed with water, brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto yield a yellow oil

Sources & evidence

ORD record
ord-c69feec9fa6044c0b8717530f36ac7ff
Source dataset
uspto-grants-2011_01
Patent number
US07868030B2

Reaction notes

Loading…