Tetrahydrofuran → HCID 72728038, compound

HRID 914729Notes

Reaction equation

HRID 914729 reaction equation
[CH2:1]1[O:11][C:10]2[C:3](=[C:4]([CH:7]=[CH:8][CH:9]=2)[CH:5]=O)[O:2]1.C1C[O:15][CH2:14][CH2:13]1>C(OCC)C.O.[Zn+2].[Br-].[Br-].[Cl-].[Cl-].[Zn+2]>[CH2:1]1[O:11][C:10]2[C:3](=[C:4]([CH:5]=[CH:13][CH:14]=[O:15])[CH:7]=[CH:8][CH:9]=2)[O:2]1

Participants

6

Reactant 2

HCID 8028TetrahydrofuranHCID 822641,3-Benzodioxole-4-carboxaldehyde

Product 1

HCID 72728038HCID 72728038, compound

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 10421208Zinc bromideCatalystHCID 21584184Diethylether waterSolvent

Conditions

Temperature
10 °C

Procedure

To a solution of 2,3-methylenedioxybenzaldehyde (150 mg) in 5 mL THF was added 22 mg of ZnBr2. With stirring, 250 mg of α,α-bis(trimethylsilyl)-t-butylacetaldimine (7) was added, and stirring was continued overnight. The solution was cooled to 10° C., then hydrolyzed by the addition of a solution of ZnCl2 (22 mg) in diethyl ether/water (5 mL each), followed by stirring at room temperature for 1 h. The solids were removed by filtration through Celite and the filtrate extracted with diethyl ether (2×). The combined ether extracts were washed with water and brine, dried over magnesium sulfate, filtered and concentrated to provide the title compound as a brown oil (150 mg): 1H NMR (CDCl3) δ 6.09 (s, 2H), 6.14 (s, 1H), 6.86-6.98 (m, 4H), 7.43 (d, 1H, J=9.6 Hz), 9.69 (d, 1H, J=4.5 Hz).

Workup

  1. stirringstirring
  2. stirringby stirring at room temperature for 1 h
  3. customThe solids were removed by filtration through Celite
  4. extractionthe filtrate extracted with diethyl ether (2×)
  5. washThe combined ether extracts were washed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-00ad7cf320c646d1a6128cc216d413f3
Source dataset
uspto-grants-2007_09
Patent number
US07265112B2

Reaction notes

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