Acetonitrile → HCID 67780233, compound

HRID 1648039Notes

Reaction equation

HRID 1648039 reaction equation
[OH:1][C:2]1[CH:13]=[CH:12][CH:11]=[CH:10][C:3]=1[CH:4]=[CH:5][C:6]([O:8][CH3:9])=[O:7].[Br:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]Br.C(=O)([O-])[O-].[K+].[K+].C(#N)C>CCOCC>[CH3:9][O:8][C:6](=[O:7])/[CH:5]=[CH:4]/[C:3]1[CH:10]=[CH:11][CH:12]=[CH:13][C:2]=1[O:1][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][Br:14]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 81001,5-DibromopentaneHCID 11430Potassium CarbonateHCID 89400Methyl 3-(2-hydroxyphenyl)prop-2-enoate

Product 1

HCID 67780233HCID 67780233, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 0.64 g (3.59 mmol) of methyl 2-hydroxycinnamate, 6.6. g (28.7 mmol) of 1,5-dibromopentane, 2 g (14.5 mmol) of anhydrous, granular potassium carbonate, and 25 mL of acetonitrile was stirred and refluxed for 24 hr. The resulting slurry was cooled, diluted with ether, and filtered with suction. The solids were washed well with ether. The filtrate and washes were combined and concentrated under reduced pressure. The oily residue was flash chromatographed on silica gel, eluting with 5:1 hexane-ether giving 1 g (85%) of (E)-3-[2-[(5-bromopentyl)oxy]phenyl]-2-propenoic acid methyl ester as a solid.

Workup

  1. temperaturerefluxed for 24 hr
  2. temperatureThe resulting slurry was cooled
  3. filtrationfiltered with suction
  4. washThe solids were washed well with ether
  5. concentrationconcentrated under reduced pressure
  6. customchromatographed on silica gel
  7. washeluting with 5:1 hexane-ether giving 1 g (85%) of (E)-3-[2-[(5-bromopentyl)oxy]phenyl]-2-propenoic acid methyl ester as a solid

Sources & evidence

ORD record
ord-4b04de0c88e849b286261ca1976ebfed
Source dataset
uspto-grants-1995_07
Patent number
US05434186

Reaction notes

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