Potassium Carbonate → HCID 54312387, compound

HRID 2242359Notes

Reaction equation

HRID 2242359 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=[O:7].S([CH2:21][N+:22]#[C-:23])(C1C=CC(C)=CC=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CO>[O:7]1[C:6]([C:5]2[CH:4]=[C:3]([CH2:2][OH:1])[CH:10]=[CH:9][CH:8]=2)=[CH:23][N:22]=[CH:21]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 161915Tosylmethyl isocyanideHCID 131314553-(Hydroxymethyl)benzaldehyde

Product 1

HCID 54312387HCID 54312387, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-Hydroxymethyl-benzaldehyde (1.14 g, 8.35 mmol), tosylmethyl isocyanide (2.47 g, 12.5 mmol) and potassium carbonate (1.75 g, 12.5 mmol) in methanol (25 ml) were refluxed at 85° C. for 1 h. The reaction was concentrated, residue dissolved in DCM/water and separated using a hydrophobic filter tube. The organic phase was concentrated and purified by silica chromatography using DCM followed by DCM:MeOH (19:1) to yield (3-oxazol-5-yl-phenyl)methanol (1.32 g, 90%) as an orange oil.

Workup

  1. concentrationThe reaction was concentrated
  2. dissolutionresidue dissolved in DCM/water
  3. customseparated
  4. concentrationThe organic phase was concentrated
  5. custompurified by silica chromatography

Sources & evidence

ORD record
ord-b79c986f90e946b093d0e00b799bfa22
Source dataset
uspto-grants-2010_03
Patent number
US07671080B2

Reaction notes

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