Water → HCID 13679816, compound

HRID 2298356Notes

Reaction equation

HRID 2298356 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[N+]([C:13]1[S:17][C:16]([CH:18]=[O:19])=[CH:15][CH:14]=1)([O-])=O.O>CS(C)=O>[O:7]([C:13]1[S:17][C:16]([CH:18]=[O:19])=[CH:15][CH:14]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 996PhenolHCID 24758Sodium hydrideHCID 782815-Nitrothiophene-2-carboxaldehyde

Product 1

HCID 13679816HCID 13679816, compoundYield 5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Phenol (3.3 g, 35 mmol) is added in portions to a suspension of 60% NaH (1.3 g, 35 mmol) in DMSO (100 mL). The resulting mixture is stirred for 30 minutes then 5-nitrothiophene-2-carboxaldehyde (5 g, 32 mmol) is added. After 1 hour the reaction mixture is poured into water (1 L) and washed with ether (4×500 mL). The combined organic layers are dried over Na2SO4, filtered and evaporated to dryness. The resulting material is dissolved in MeOH and passed through a column (2.5 cm×20 cm) of Amberjet 4400 (OH− form). The eluent is dried in vacuo then evaporated twice from CH3CN. The crude product is purified by column chromatography in EtOAc-hexanes (1:1) to yield the desired aldehyde (304 mg, 5%). 1H NMR (300 MHz, CDCl3) δ 6.52, 7.20, 7.27, 7.45, 7.55, 9.75.

Workup

  1. washwashed with ether (4×500 mL)
  2. dry with materialThe combined organic layers are dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated to dryness
  5. dissolutionThe resulting material is dissolved in MeOH
  6. customThe eluent is dried in vacuo
  7. customthen evaporated twice from CH3CN
  8. customThe crude product is purified by column chromatography in EtOAc-hexanes (1:1)

Sources & evidence

ORD record
ord-60a16f12007b451fa0724118682d1508
Source dataset
uspto-grants-2002_12
Patent number
US06492385B2

Reaction notes

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