HCID 11617199, compound → Diphenyl Ether

HRID 1443079Notes

Reaction equation

HRID 1443079 reaction equation
Br[C:2]1[CH:21]=[CH:20][CH:19]=[CH:18][C:3]=1[O:4][CH:5]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14]C=1)[CH:6]1[O:11][CH2:10][CH2:9][NH:8][CH2:7]1>C1(C)C=CC=CC=1.COCCO[AlH2-]OCCOC.[Na+]>[NH:8]1[CH2:9][CH2:10][O:11][CH2:6][CH2:7]1.[C:5]1([O:4][C:3]2[CH:2]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:12]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 1

HCID 11617199HCID 11617199, compound

Product 2

HCID 7583Diphenyl EtherYield 48.6%HCID 8083Morpholine

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 16684438Red-AlSolvent

Procedure

To a solution of morpholinone 2 (0.214 g, 0.750 mmol) in toluene (10 mL), Red-Al (65% solution in toluene, 1.5 mL) was added dropwise at 0° C. The reaction mixture was stirred at ice temperature for 4 h. Excess Red-Al was destroyed by dropwise addition of 2M NaOH solution (5 mL) and acidified to pH 2 with 6N HCl. The solution was neutralized with saturated NaHCO3 and extracted with toluene (2×10 mL). The combined organic extract was washed with brine and dried over anhydrous Na2SO4. The solvent was removed under reduced pressure and the product was purified on a column of silica gel (ethyl acetate: methanol, 80:20) to give morpholine compound 3 as a colorless solid (Yield: 0.062 g, 31%), mp 156-158° C. 1H NMR (CDCl3) δ: 7.45-7.38 (m, 5H), 6.97 (m, 2H), 6.58 (m, 1H), 6.50 (d, 1H), 4.53 (d, 1H), 4.10 (m, 1H), 3.95 (m, 1H), 3.90 (m, 1H), 2.90 (m, 2H), 2.50 (m, 1H), 2.42 (m, 1H). MS (ES) m/z 285.98 [C17H19NO3+H]+. Analysis: Calcd for C17H19NO3 (0.5H2O) C, 69.37; H, 6.85; N, 4.76. Found: C, 69.68; H, 5.45; N, 4.44.

Workup

  1. customExcess Red-Al was destroyed by dropwise addition of 2M NaOH solution (5 mL)
  2. extractionextracted with toluene (2×10 mL)
  3. extractionThe combined organic extract
  4. washwas washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. customThe solvent was removed under reduced pressure
  7. customthe product was purified on a column of silica gel (ethyl acetate: methanol, 80:20)

Sources & evidence

ORD record
ord-386efc25b94145f992303497714f04c0
Source dataset
uspto-grants-2010_02
Patent number
US07659394B2

Reaction notes

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