Potassium Carbonate → 8-(4-Methoxyphenyl)-1,4-dioxaspiro[4.5]dec-7-ene

HRID 604666Notes

Reaction equation

HRID 604666 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.FC(F)(F)S(O[C:18]1[CH2:27][CH2:26][C:21]2([O:25][CH2:24][CH2:23][O:22]2)[CH2:20][CH:19]=1)(=O)=O.C([O-])([O-])=O.[K+].[K+]>[Pd](Cl)Cl.C(P(C(C)(C)C)[C-]1C=CC=C1)(C)(C)C.[C-]1(P(C(C)(C)C)C(C)(C)C)C=CC=C1.[Fe+2].C1COCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:18]2[CH2:27][CH2:26][C:21]3([O:25][CH2:24][CH2:23][O:22]3)[CH2:20][CH:19]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 114830861,4-Dioxaspiro[4.5]dec-7-en-8-yl trifluoromethanesulfonate

Product 1

HCID 148634918-(4-Methoxyphenyl)-1,4-dioxaspiro[4.5]dec-7-ene

Reagents, catalysts & solvents 2

HCID 178454861HCID 178454861, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A flask was charged with (4-methoxyphenyl)boronic acid (515 mg, 3.39 mmol), 1,4-dioxaspiro[4.5]dec-7-en-8-yl trifluoromethanesulfonate (780 mg, 2.71 mmol), 1,1′-bis(di-t-butylphosphino)ferrocene palladium dichloride (35 mg, 0.054 mmol), 1M K2CO3 (10 mL, 10 mmol), and THF (10 mL). The reaction was degassed with N2 and heated to 50° C. for 16 hours. The reaction was cooled to room temperature and diluted with EtOAc (100 mL). The mixture was washed with water (2×25 mL) and brine (2×25 mL), and the organic layer was dried (Na2SO4), filtered, and concentrated. Purification of the residue by flash chromatography on silica gel (5 to 40% EtOAc/hexanes) afforded 8-(4-methoxyphenyl)-1,4-dioxaspiro[4.5]dec-7-ene. Rf=0.20 (25% EtOAc/hexanes). 1H NMR (500 MHz, CDCl3): δ 7.31-7.34 (m, 2H), 6.82-6.85 (m, 2H), 5.90 (m, 1H), 4.02 (s, 4H), 3.80 (s, 3H), 2.62-2.66 (m, 2H), 2.45-2.46 (m, 2H), 1.92 (t, J=6.5 Hz, 2H).

Workup

  1. customThe reaction was degassed with N2
  2. temperatureThe reaction was cooled to room temperature
  3. additiondiluted with EtOAc (100 mL)
  4. washThe mixture was washed with water (2×25 mL) and brine (2×25 mL)
  5. dry with materialthe organic layer was dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification of the residue by flash chromatography on silica gel (5 to 40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-a8b3eed2f552444096a3ac5f41a2d812
Source dataset
uspto-grants-2011_03
Patent number
US07910592B2

Reaction notes

Loading…