Tetrahydrofuran → 5-(4-Fluorophenoxy)-2-thiophenecarboxaldehyde

HRID 1694014Notes

Reaction equation

HRID 1694014 reaction equation
[O:1]1CCCC1.[F:6][C:7]1[CH:20]=[CH:19][C:10]([O:11][C:12]2[S:16][C:15]([C:17]#N)=[CH:14][CH:13]=2)=[CH:9][CH:8]=1.[H-].C([Al+]CC(C)C)C(C)C>O>[F:6][C:7]1[CH:20]=[CH:19][C:10]([O:11][C:12]2[S:16][C:15]([CH:17]=[O:1])=[CH:14][CH:13]=2)=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 21225700DiisobutylaluminumhydrideHCID 231305625-(4-Fluorophenoxy)thiophene-2-carbonitrile

Product 1

HCID 194222425-(4-Fluorophenoxy)-2-thiophenecarboxaldehydeYield 55%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a tetrahydrofuran (150 mL) solution of 5-(4-fluoro-phenoxy)-thiophene-2-carbonitrile (6.10 g, 27.8 mmol) described in Manufacturing Example 91-1-1 was added dropwise diisobutyl aluminum hydride (0.97 M n-hexane solution, 43.0 mL, 41.7 mmol) on a dry ice-ethanol bath (−78° C.) under nitrogen atmosphere, which was stirred for 2 hours at room temperature. The reaction solution was added to water, followed by extraction with ethyl acetate. 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 (3.4 g, 55.0%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium chloride
  3. customthe solvent was evaporated under a reduced pressure
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate:heptane=1:5)

Sources & evidence

ORD record
ord-71e72dcc667c49d49db5fe2f472c1e29
Source dataset
uspto-grants-2012_04
Patent number
US08158657B2

Reaction notes

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