Water → HCID 13679816, compound

HRID 1359637Notes

Reaction equation

HRID 1359637 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-cc3662f2d1cd45d89825ab04ff88d1be
Source dataset
uspto-grants-2003_07
Patent number
US06599916B2

Reaction notes

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