4-Methoxybenzyl alcohol → HCID 67814067, compound

HRID 1772320Notes

Reaction equation

HRID 1772320 reaction equation
[H-].[Na+].C1COCC1.[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][OH:17])=[CH:12][CH:11]=1.Cl[CH2:19][C:20]1[CH:24]=[C:23]([CH3:25])[O:22][N:21]=1>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl-].[NH4+]>[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][O:17][CH2:19][C:20]2[CH:24]=[C:23]([CH3:25])[O:22][N:21]=2)=[CH:12][CH:11]=1

Participants

7

Reactant 4

HCID 77384-Methoxybenzyl alcoholHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 27357633-(Chloromethyl)-5-methyl-1,2-oxazole

Product 1

HCID 67814067HCID 67814067, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 25517Ammonium ChlorideSolvent

Procedure

To a resealable vial were added NaH (193 mg, 60% dispersion in mineral oil, 4.82 mmol) and THF. The vial was cooled to 0° C. before addition of (4-methoxyphenyl)methanol (639 μl, 5.14 mmol) and the reaction stirred at 0° C. for 30 min before addition of 3-(chloromethyl)-5-methylisoxazole (423 mg, 3.22 mmol) and tetrabutylammonium iodide (119 mg, 0.322 mmol). The reaction was heated to reflux overnight. The vial was cooled to room temperature before being diluted with ammonium chloride solution. The aqueous was extracted with EtOAc and the combined organics were washed with brine, dried over Na2SO4, filtered, and concentrated. The crude residue was purified via Biotage (EtOAc/hex) to afford 3-((4-methoxybenzyloxy)methyl)-5-methylisoxazole. m/z (ESI) 256 [M+Na]+.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux overnight
  3. extractionThe aqueous was extracted with EtOAc
  4. washthe combined organics were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude residue was purified via Biotage (EtOAc/hex)

Sources & evidence

ORD record
ord-da8e6679cb4e4282929750c8fb77c2ef
Source dataset
uspto-grants-2016_02
Patent number
US09249161B2

Reaction notes

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