2-Hexynoic acid → HCID 18008055, compound

HRID 988245Notes

Reaction equation

HRID 988245 reaction equation
I[C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[O:5][CH2:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=1.[C:20]([OH:27])(=[O:26])[C:21]#[C:22][CH2:23][CH2:24][CH3:25]>N1CCCCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:15]=[CH:16][C:7]=1[CH2:6][O:5][C:4]1[CH:3]=[C:2]([C:25]#[C:24][CH2:23][CH2:22][CH2:21][C:20]([OH:27])=[O:26])[CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 2

HCID 3243802-Hexynoic acidHCID 18008068HCID 18008068, compound

Product 1

HCID 18008055HCID 18008055, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8082PiperidineSolvent

Conditions

Temperature
75 °C

Procedure

A solution of 2-(3-iodophenoxymethyl)-naphthalene (0.5 g, 1.4 mmol) and hexynoic acid (0.19 g, 1.7 mmol) in piperidine (5 mL) is purged with Argon for 20 minutes. Then bis(triphenylphosphine)palladium dichloride (0.01 g, 0.014 mmol) and cuprous iodide (0.005 g, 0.028 mmol) are added and this mixture heated in an oil bath at 75° C. for 1.5 hours and then allowed to come to room temperature overnight. The solvent was removed in vacuo and the residue purified by flash chromatography (silica, 4% methanol in dichloromethane) to give the title compound. 1H NMR (300 MHz, CDCl3) δ 7.83-7.88 (m, 4H), 7.48-7.54 (m, 3H), 7.19 (t, 1H), 6.98-7.05 (m, 3H), 5.21 (s, 2H), 2.47 (t, 2H), 1.80-1.91 (m, 4H); MS (EI) 344 (M)+.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue purified by flash chromatography (silica, 4% methanol in dichloromethane)

Sources & evidence

ORD record
ord-526e984603984e6a97d5102c1e69a371
Source dataset
uspto-grants-2003_10
Patent number
US06635655B1

Reaction notes

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