Tetrahydrofuran → 5-p-Tolyloxy-thiophene-2-carbaldehyde

HRID 77916Notes

Reaction equation

HRID 77916 reaction equation
[C:1]1([CH3:15])[CH:6]=[CH:5][C:4]([O:7][C:8]2[S:12][C:11]([C:13]#N)=[CH:10][CH:9]=2)=[CH:3][CH:2]=1.[H-].C([Al+]CC(C)C)C(C)C.[O:26]1CCCC1>>[C:1]1([CH3:15])[CH:6]=[CH:5][C:4]([O:7][C:8]2[S:12][C:11]([CH:13]=[O:26])=[CH:10][CH:9]=2)=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 21225700DiisobutylaluminumhydrideHCID 231303655-p-Tolyloxy-thiophene-2-carbonitrile

Product 1

HCID 592554125-p-Tolyloxy-thiophene-2-carbaldehydeYield 47.2%

Procedure

To a tetrahydrofuran (70.0 mL) solution of 5-p-tolyloxy-thiophene-2-carbonitrile (2.00 g, 9.29 mmol) described in Manufacturing Example 48-1-1 was added dropwise diisobutyl aluminum hydride (0.97 M n-hexane solution, 23.9 mL, 23.2 mmol) on a dry ice-ethanol bath (−78° C.) under nitrogen atmosphere, which was stirred for 3 hours at room temperature. The reaction mixture was cooled to room temperature and extracted with ethyl acetate after addition of water. The organic layer was washed with saturated aqueous sodium chloride, and the solvent was evaporated under a reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:heptane=1:5) to obtain the title compound (958 mg, 47.2%).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. additionafter addition of water
  4. washThe organic layer was washed with saturated aqueous sodium chloride
  5. customthe solvent was evaporated under a reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate:heptane=1:5)

Sources & evidence

ORD record
ord-9d3788c83b5145019c45d35ba4d445ca
Source dataset
uspto-grants-2014_09
Patent number
US08841327B2

Reaction notes

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