Ammonium Chloride → HCID 67460487, compound

HRID 554508Notes

Reaction equation

HRID 554508 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[C:10]=1[CH:11]=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[NH4+]>C1COCC1>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[C:10]=1[CH:11]([C:14]1[CH:15]=[CH:16][C:9]([O:8][CH3:1])=[CH:10][CH:13]=1)[OH:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 25517Ammonium ChlorideHCID 21904960HCID 21904960, compound

Product 1

HCID 67460487HCID 67460487, compoundYield 170.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a THF solution (50 mL) of 2-benzyloxy-6-fluoro-benzaldehyde (2.25 g, 9.8 mmol) as described in International Publication WO 04/048335, a 4-methoxyphenyl-magnesium bromide THF solution (0.5 M, 21.5 mL) was added dropwise in a nitrogen stream at room temperature. The reaction mixture was stirred at room temperature for 1.5 hours, and then a saturated ammonium chloride aqueous solution was added thereto under cooling with ice and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution and dried (anhydrous magnesium sulfate), and then the solvent was distilled under reduced pressure. The obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:5)] to obtain the title compound (2.82 g, 85%).

Workup

  1. temperatureunder cooling with ice
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  4. dry with materialdried (anhydrous magnesium sulfate)
  5. distillationthe solvent was distilled under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:5)]

Sources & evidence

ORD record
ord-923f0c65af874f518d7e0b487f53deba
Source dataset
uspto-grants-2011_11
Patent number
US08048897B2

Reaction notes

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