1,4-Dioxane → Ketone, 3-furyl phenyl

HRID 1840138Notes

Reaction equation

HRID 1840138 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][CH:15]=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][CH:15]=1)[CH:11]=[O:12]

Participants

7

Reactant 4

HCID 312751,4-DioxaneHCID 765833-BromobenzaldehydeHCID 522689Potassium FluorideHCID 43936882-(Tributylstannyl)furan

Product 1

HCID 201640Ketone, 3-furyl phenylYield 86%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

EX-592A) To a dioxane (20 mL) solution of 3-bromobenzaldehyde (0.63 mL, 5.4 mmol) was added 2-(tributylstannyl)furan (1.89 mL, 6.00 mL) and Pd(PPh3)2Cl2 (0.21 g, 0.30 mmol). The mixture was heated to reflux under argon for 1.5 h. The cooled mixture was poured into a mixture of saturated KF and ethyl acetate and stirred 18 h. The slurry was filtered through celite. The organic layer was separated, washed with brine, dried (MgSO4) and evaporated to an oil. Purification by flash chromatography on silica gel eluting with 5% ethyl acetate in hexane gave 0.80 g (86%) of the desired 3-(2-furanyl)benzaldehyde product as an yellow oil which solidified upon standing. MS: m/z =173.1 [M+H]+.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux under argon for 1.5 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 an oil
  8. customPurification by flash chromatography on silica gel eluting with 5% ethyl acetate in hexane

Sources & evidence

ORD record
ord-94f5677f76704cf3ad1fefbe722fdd83
Source dataset
uspto-grants-2004_01
Patent number
US06677380B2

Reaction notes

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