Tetrahydrofuran → HCID 67460494, compound

HRID 554488Notes

Reaction equation

HRID 554488 reaction equation
CCCCCC.C([Li])CCC.[CH2:12]([O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[F:27][C:28]([F:39])([F:38])[O:29][C:30]1[CH:37]=[CH:36][C:33](C=O)=[CH:32][CH:31]=1.[Cl-].[NH4+].C1C[O:45][CH2:44]C1>>[CH2:12]([O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH:44]([C:37]1[CH:36]=[CH:33][CH:32]=[CH:31][C:30]=1[O:29][C:28]([F:27])([F:38])[F:39])[OH:45])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 5

HCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 69573p-(Trifluoromethoxy)benzaldehydeHCID 5618281-(Benzyloxy)-2-bromobenzeneHCID 178418244HCID 178418244, compound

Product 1

HCID 67460494HCID 67460494, compoundYield 77%

Procedure

In a nitrogen stream, an n-butyllithium hexane solution (1.59 M, 8.7 mL) was added dropwise to a solution of 1-benzyloxy-2-bromobenzene (3.3 g, 12.64 mmol) in THF (126 mL) at −78° C. and the mixture solution was stirred at the same temperature for 15 minutes. To this solution, a solution of 4-trifluoromethoxybenzaldehyde (2.0 g, 10.52 mmol) in THF (42 mL) was added dropwise at −78° C. The reaction mixture was stirred at the same temperature for 40 minutes and at 0° C. for 45 minutes, and then a saturated ammonium chloride aqueous solution was added thereto 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 (1:10)] to obtain the title compound (3.03 g, 77%) as a colorless oil.

Workup

  1. stirringThe reaction mixture was stirred at the same temperature for 40 minutes and at 0° C. for 45 minutes
  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 (1:10)]

Sources & evidence

ORD record
ord-25055188e7174b4095e7a74e0901aadc
Source dataset
uspto-grants-2011_11
Patent number
US08048897B2

Reaction notes

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