1,4-Dioxane → 3-(2-Furanyl)4-(4-morpholinyl)benzaldehyde

HRID 1371075Notes

Reaction equation

HRID 1371075 reaction equation
[O:1]1[CH2:6][CH2:5]O[CH2:3][CH2:2]1.Br[C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][C:15]=1[N:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1)[CH:11]=[O:12].C([Sn](CCCC)(CCCC)C1OC=CC=1)CCC.[F-].[K+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(OCC)(=O)C>[O:1]1[CH:6]=[CH:5][CH:3]=[C:2]1[C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][C:15]=1[N:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1)[CH:11]=[O:12]

Participants

7

Reactant 4

HCID 312751,4-DioxaneHCID 522689Potassium FluorideHCID 43936882-(Tributylstannyl)furanHCID 235060203-Bromo-4-morpholinobenzaldehyde

Product 1

HCID 235060363-(2-Furanyl)4-(4-morpholinyl)benzaldehydeYield 84%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

EX-604B) To a dioxane (8 mL) solution of the aldehyde from EX-604A (0.77 g, 2.8 mmol) was added 2-(tributylstannyl)furan (1.07 mL, 3.42 mmol) and Pd(PPh3)2Cl2 (0.12 g, 0.17 mmol). The mixture was heated to reflux under argon for 18 h. The cooled mixture was poured into a mixture of saturated aq. KF and ethyl acetate and stirred 3 h. The slurry was filtered through celite. The organic layer was separated, washed with brine, dried (MgSO4) and evaporated to a yellow oil. Purification by silica gel flash chromatography eluting with 20% ethyl acetate in hexane gave 0.61 g (84%) of the desired 3-(2-furanyl)-4-(4-morpholinyl)benzaldehyde product as a yellow oil. MS: m/z=258.1 [M+H]+.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux under argon for 18 h
  3. filtrationThe slurry was filtered through celite
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. customevaporated to a yellow oil
  8. customPurification by silica gel flash chromatography
  9. washeluting with 20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-d4c1267cd8674aa1a82f43e95bf86d44
Source dataset
uspto-grants-2003_06
Patent number
US06583183B2

Reaction notes

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