Water → HCID 19606329, compound

HRID 1603892Notes

Reaction equation

HRID 1603892 reaction equation
[H-].[K+].[OH:3][CH2:4][C:5]1[O:6][C:7]2[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][C:8]=2[CH:9]=1.[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O>CCCCCC.C1C=CC=CC=1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:16]([O:3][CH2:4][C:5]1[O:6][C:7]2[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][C:8]=2[CH:9]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

8

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 82127Potassium hydrideHCID 12813635HCID 12813635, compound

Product 1

HCID 19606329HCID 19606329, compoundYield 82%

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 241BenzeneSolvent2×HCID 8058HexaneSolvent

Procedure

A dispersion of potassium hydride (0.990 g, 5.04 mmol) in 20% mineral oil was washed by decantation with anhydrous hexane, then was resuspended in anhydrous benzene (25 ml). This suspension was added at 0° C. and under inert atmosphere with a solution of 2-(hydroxymethyl)benzofuran-5-carbonitrile (0.671 mg, 3.89 mmol) in benzene (10 ml) stirring at room temperature for 15 min, then with benzyl bromide (0.825 ml) and a catalytic amount of tetrabutylammonium iodide. The mixture was left under stirring at room temperature for 4 h, then added with water (50 ml) and extracted with ethyl acetate (4×50 ml). The organic phase was dried and the solvent removed, to obtain a crude which was purified by chromatography through a silica gel column, eluting with n-hexane:ethyl acetate mixtures of increasing polarity, thereby recovering 1.087 g of the title compound as a yellowish oil (82% yield).

Workup

  1. waitThe mixture was left
  2. stirringunder stirring at room temperature for 4 h
  3. extractionextracted with ethyl acetate (4×50 ml)
  4. customThe organic phase was dried
  5. customthe solvent removed
  6. customto obtain a crude which
  7. customwas purified by chromatography through a silica gel column
  8. washeluting with n-hexane
  9. temperatureethyl acetate mixtures of increasing polarity

Sources & evidence

ORD record
ord-24500f52f75d4906a12f0325de55140f
Source dataset
uspto-grants-1999_11
Patent number
US05990142

Reaction notes

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