Potassium Iodide → HCID 45280396, compound

HRID 422866Notes

Reaction equation

HRID 422866 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][CH:29]=1)[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]2([CH2:18][O:17][C:16]3[CH:19]=[C:20]4[C:24](=[CH:25][C:15]2=3)[CH2:23][CH2:22][O:21]4)[C:7]1=[O:26].C(=O)([O-])[O-].[K+].[K+].Br[CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39].[I-].[K+]>CN(C)C=O.C(OCC)(=O)C.O>[O:26]=[C:7]1[C:8]2([CH2:18][O:17][C:16]3[CH:19]=[C:20]4[C:24](=[CH:25][C:15]2=3)[CH2:23][CH2:22][O:21]4)[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:6]1[CH2:5][C:4]1[CH:3]=[C:2]([CH:29]=[CH:28][CH:27]=1)[O:1][CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39]

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 593525401'-(3-hydroxybenzyl)-5,6-dihydrospiro[benzo[1,2-b:5,4-b']difuran-3,3'-indol]-2'(1'H)-one

Product 1

HCID 45280396HCID 45280396, compoundYield 93.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

To a stirred solution of 1′-(3-hydroxybenzyl)-5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indol]-2′(1′H)-one (0.46 g, 1.18 mmol) in N,N-dimethylformamide (4 mL) were added potassium carbonate (0.32 g, 2.36 mmol), ethyl bromoacetate (0.20 mL, 1.77 mmol), and potassium iodide (0.024 g, 0.14 mmol) at ambient temperature. The mixture was stirred at 40° C. for 16 h. Water (50 mL) and ethyl acetate (150 mL) were added to the mixture. The organic solution was separated and the aqueous layer was extracted with ethyl acetate (2×80 mL). The combined organic solution was washed with brine (100 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified by column chromatography (hexanes/ethyl acetate from 2:1 to 1:1) to afford ethyl {3-[(2′-oxo-5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indol]-1′(2′H)-yl)methyl]phenoxy}acetate (0.52 g, 93%): mp 45-46° C.; 1H NMR (300 MHz, CDCl3) δ 7.30-7.15 (m, 3H), 7.06-6.96 (m, 2H), 6.90 (br s, 1H), 6.84-6.76 (m, 2H), 6.50 (s, 1H), 6.43 (s, 1H), 5.07-4.96 (m, 2H), 4.87-4.78 (m, 1H), 4.75-4.68 (m, 1H), 4.60-4.50 (m, 4H), 4.22 (q, J=7.1 Hz, 2H), 3.11-2.91 (m, 2H), 1.26 (t, J=7.1 Hz, 3H); 13C NMR (75 MHz, CDCl3) δ 177.9, 168.7, 161.8, 161.3, 158.2, 142.0, 137.6, 132.7, 130.0, 128.7, 123.8, 123.4, 120.7, 120.2, 119.9, 118.9, 114.0, 113.7, 109.2, 93.2, 80.6, 72.4, 65.4, 61.4, 57.7, 44.0, 29.0, 14.1; MS (ES+) m/z 471.9 (M+1).

Workup

  1. customThe organic solution was separated
  2. extractionthe aqueous layer was extracted with ethyl acetate (2×80 mL)
  3. washThe combined organic solution was washed with brine (100 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography (hexanes/ethyl acetate from 2:1 to 1:1)

Sources & evidence

ORD record
ord-a0c53a2f00274e46bf54413300a28378
Source dataset
uspto-grants-2012_01
Patent number
US08101647B2

Reaction notes

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