Propargyl alcohol → (4,6-Dichlorobenzofuran-2-yl)methanol

HRID 710302Notes

Reaction equation

HRID 710302 reaction equation
[CH2:1]([OH:4])[C:2]#[CH:3].[Cl:5][C:6]1[C:7](I)=[C:8]([OH:13])[CH:9]=[C:10]([Cl:12])[CH:11]=1>N1C=CC=CC=1>[Cl:5][C:6]1[C:7]2[CH:3]=[C:2]([CH2:1][OH:4])[O:13][C:8]=2[CH:9]=[C:10]([Cl:12])[CH:11]=1

Participants

4

Reactant 2

HCID 7859Propargyl alcoholHCID 401517703,5-Dichloro-2-iodophenol

Product 1

HCID 65440707(4,6-Dichlorobenzofuran-2-yl)methanolYield 56.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Propargyl alcohol (0.12 ml; 1.96 mmol) was added drop wise to a refluxing mixture of the product of Step D (0.55 g; 1.96 mmol) and Cu2O (0.2 g; 1.4 mmol) in anhydrous pyridine (4 ml) under N2. After refluxing for 1 h, the solvent was removed under reduced pressure and the residue was treated with EtOAc (15 ml). The insoluble material was filtered off and the filtrate was washed with 10% citric acid, H2O, brine, dried over anhydrous MgSO4 and filtered. The filtrate was evaporated under reduced pressure and the residue was purified by FCC (SiO2; CH2Cl2) to give the title compound (0.24 g; 56%) as colourless solid. 1H-NMR (CDCl3) 1.91 (tr, 1H, J=6.3 Hz); 4.75 (d, 1H, J=6.3 Hz); 6.72 (s, 1H); 7.23 (s, 1H); 7.37 (s, 1H).

Workup

  1. temperatureAfter refluxing for 1 h
  2. customthe solvent was removed under reduced pressure
  3. additionthe residue was treated with EtOAc (15 ml)
  4. filtrationThe insoluble material was filtered off
  5. washthe filtrate was washed with 10% citric acid, H2O, brine
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationfiltered
  8. customThe filtrate was evaporated under reduced pressure
  9. customthe residue was purified by FCC (SiO2; CH2Cl2)

Sources & evidence

ORD record
ord-a9967b4f03bb41b698d40d76d51867d5
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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