Methyl morpholine oxide → 4-(4-Fluorophenyl)-2-oxo-2H-chromene-7-carbaldehyde

HRID 1988189Notes

Reaction equation

HRID 1988189 reaction equation
Br[CH2:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)=[CH:8][C:9](=[O:13])[O:10]2)=[CH:5][CH:4]=1.C[N+]1([O-])CC[O:25]CC1>O1CCOCC1>[F:20][C:17]1[CH:18]=[CH:19][C:14]([C:7]2[C:6]3[C:11](=[CH:12][C:3]([CH:2]=[O:25])=[CH:4][CH:5]=3)[O:10][C:9](=[O:13])[CH:8]=2)=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 82029Methyl morpholine oxideHCID 194269637-(bromomethyl)-4-(4-fluorophenyl)-2H-chromen-2-one2×

Product 1

HCID 468452294-(4-Fluorophenyl)-2-oxo-2H-chromene-7-carbaldehyde

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

7-(Bromomethyl)-4-(4-fluorophenyl)-2H-chromen-2-one can be prepared as described in Example 1A; its preparation is also described in U.S. Pat. No. 5,552,437. 7-(Bromomethyl)-4-(4-fluorophenyl)-2H-chromen-2-one (11.42 g, 34.3 mmol) and NMO (13.9 g, 102.8 mmol) in 110 mL of dioxane were heated to reflux for 6 h. The solution was cooled to rt and the solvent removed. The crude compound was diluted in EtOAc and washed with NH4Claq, water, brine and dried over MgSO4. The solvent was removed to yield the title compound. 1H NMR (400 MHz, acetone-d6): δ 10.20 (1H, s), 7.95 (1H, s), 7.85 (1H, m), 7.68 (3H, m), 7.38 (2H, m) and 6.51 (1H, s).

Workup

  1. customits preparation
  2. temperatureto reflux for 6 h
  3. customthe solvent removed
  4. additionThe crude compound was diluted in EtOAc
  5. washwashed with NH4Claq, water, brine
  6. dry with materialdried over MgSO4
  7. customThe solvent was removed

Sources & evidence

ORD record
ord-8af8a55fbbc346c7bdcfb048aa957b17
Source dataset
uspto-grants-2009_06
Patent number
US07553973B2

Reaction notes

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