18-Crown-6 → HCID 70225107, compound

HRID 1532858Notes

Reaction equation

HRID 1532858 reaction equation
[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10]Cl)=[CH:6][C:5]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH3:18].[K].[CH2:21]([OH:27])[C:22]1[O:26][CH:25]=[CH:24][CH:23]=1.C1OCCOCCOCCOCCOCCOC1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][O:27][CH2:21][C:22]2[O:26][CH:25]=[CH:24][CH:23]=2)=[CH:6][C:5]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH3:18]

Participants

6

Reactant 3

HCID 2855718-Crown-6HCID 206999064-Chloromethyl-2-(2-methylphenyl)benzoic acid methyl esterHCID 70224869Furfuryl alcohol potassium salt

Product 1

HCID 70225107HCID 70225107, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To a stirred solution of the 4-chloromethyl-2-(2-methylphenyl)benzoic acid methyl ester (1.12 g , 4.08 mmol) in toluene (20 mL) under N2 was added the furfuryl alcohol potassium salt prepared in Example 299A (0.84 g, 6.1 mmol) followed by 18-crown-6 (1.6 g, 6.1 mmol). The solution was heated at 90° C. for 30 minutes. The reaction mixture was cooled to ambient temperature, diluted with ethyl acetate and washed with H2O (2×), saturated NaHCO3 solution (2×), dried (MgSO4) and concentrated in vacuo. The residue was purified by flash chromatography (10% ethyl acetate-hexane) to give the title compound (0.45 g, 33%) as an orange oilwhich was contaminated with ˜10% of the 2-furanmethyl ester.

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. washwashed with H2O (2×), saturated NaHCO3 solution (2×)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography (10% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-96b43a72d9294a42ba1afdf709a5fbfa
Source dataset
uspto-grants-2001_03
Patent number
US06204293B1

Reaction notes

Loading…