Sesamol → 1-(2-cyclopropylethyl)-3-hydroxy-3-(6-hydroxy-1,3-benzodioxol-5-yl)-1,3-dihydro-2H-indol-2-one

HRID 425448Notes

Reaction equation

HRID 425448 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([OH:10])=[CH:9][C:4]=2[O:3][CH2:2]1.C([Mg]Cl)(C)C.[CH:16]1([CH2:19][CH2:20][N:21]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:23](=[O:30])[C:22]2=[O:31])[CH2:18][CH2:17]1>C1COCC1.ClCCl>[CH:16]1([CH2:19][CH2:20][N:21]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:23]([OH:30])([C:7]3[C:8]([OH:10])=[CH:9][C:4]4[O:3][CH2:2][O:1][C:5]=4[CH:6]=3)[C:22]2=[O:31])[CH2:18][CH2:17]1

Participants

6

Reactant 3

HCID 68289SesamolHCID 655965701-(2-cyclopropylethyl)-1H-indole-2,3-dioneHCID 178418918HCID 178418918, compound

Product 1

HCID 588725381-(2-cyclopropylethyl)-3-hydroxy-3-(6-hydroxy-1,3-benzodioxol-5-yl)-1,3-dihydro-2H-indol-2-oneYield 76.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1,3-benzodioxol-5-ol (1.25 g, 9.06 mmol) in THF (20.0 mL) was added dropwise a solution of isopropylmagnesium chloride solution (4.53 mL, 9.06 mmol, 2.0 M in THF) at 0° C. over 5 min. The reaction mixture was stirred for 0.5 h upon which time colorless precipitate was formed. After the solvent was removed under reduced pressure, the residue was dissolved in dichloromethane (20.0 mL) and cooled to 0° C. A solution of 1-(2-cyclopropylethyl)-1H-indole-2,3-dione (1.77 g, 8.23 mmol) in dichloromethane (20.0 mL) was added to the above solution at 0° C. The resulting mixture was stirred at ambient temperature for 16 h and quenched with saturated ammonium chloride solution (30.0 mL). The organic layer was separated and washed with water (3×25.0 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to dryness. The residue was crystallized from ethyl acetate and ether to give the title compound (2.22 g, 76%) as a colorless solid: 1H NMR (300 MHz, CDCl3) δ 9.52 (s, 1H), 7.46 (d, 1H), 7.37 (dt, 1H), 7.18 (dt, 1H), 6.90 (d, 1H), 6.56 (s, 1H), 6.23 (s, 1H), 5.84 (dd, 2H), 4.55 (s, 1H), 3.87-3.63 (m, 2H), 1.64-1.44 (m, 2H), 0.68-0.55 (m, 1H), 0.41-0.27 (m, 2H), −0.02-(−0.07) (m, 2H); 13C NMR (75 MHz, CDCl3) δ 179.1, 152.4, 148.8, 142.7, 141.3, 130.3, 129.1, 126.3, 123.7, 117.3, 109.5, 106.9, 101.9, 101.4, 79.3, 40.6, 32.2, 8.6, 4.3, 4.2; MS (ES+) m/z 337.6 (M−17).

Workup

  1. customwas formed
  2. customAfter the solvent was removed under reduced pressure
  3. dissolutionthe residue was dissolved in dichloromethane (20.0 mL)
  4. stirringThe resulting mixture was stirred at ambient temperature for 16 h
  5. customquenched with saturated ammonium chloride solution (30.0 mL)
  6. customThe organic layer was separated
  7. washwashed with water (3×25.0 mL)
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated in vacuo to dryness
  11. customThe residue was crystallized from ethyl acetate and ether

Sources & evidence

ORD record
ord-e029224f46d44ca49a55066c268e2a4a
Source dataset
uspto-grants-2012_01
Patent number
US08106087B2

Reaction notes

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