Water → 5-(4-Isopropoxyphenoxy)thiophene-2-carbaldehyde

HRID 404910

Reaction equation

HRID 404910 reaction equation
[H-].[Na+].[CH:3]([O:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)([CH3:5])[CH3:4].[N+]([C:17]1[CH:18]=[C:19]([CH:22]=[O:23])[S:20][CH:21]=1)([O-])=O.O>CS(C)=O>[CH:3]([O:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][C:21]2[S:20][C:19]([CH:22]=[O:23])=[CH:18][CH:17]=2)=[CH:9][CH:8]=1)([CH3:5])[CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 820014-IsopropoxyphenolHCID 8188574-Nitrothiophene-2-carbaldehyde

Product 1

HCID 877212055-(4-Isopropoxyphenoxy)thiophene-2-carbaldehydeYield 7.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

NaH (60%, 480 mg, 12.0 mmol) was added in several portions to a stirred solution of Example 17A (1.52 g, 10.0 mmol) in DMSO (15 mL) at room temperature. After 20 min, 4-nitrothiophene-2-carbaldehyde (1.57 g, 10.0 mmol) was added in one portion. The mixture was stirred at room temperature for 30 minutes. The reaction mixture was poured into water, extracted with ether (2×). The ether layer was washed with 10% NaOH (1×), brine (1×), dried over MgSO4 and concentrated. The residue was purified on silica gel eluting with ethyl acetate: hexane gradient to give the desired product as a brown oil (206 mg, 7.8%).

Workup

  1. extractionextracted with ether (2×)
  2. washThe ether layer was washed with 10% NaOH (1×), brine (1×)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-3e8abb576f4a49e5b553e6cfc00ba461
Source dataset
uspto-grants-2014_06
Patent number
US08748627B2

Linked notes

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