Water → 7-methoxy-1'-pentyl-6,7-dihydrospiro[indeno[5,6-d][1,3]dioxole-5,3'-indol]-2'(1H)-one

HRID 425721Notes

Reaction equation

HRID 425721 reaction equation
[OH:1][CH:2]1[C:27]2[C:19](=[CH:20][C:21]3[O:25][CH2:24][O:23][C:22]=3[CH:26]=2)[C:4]2([C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[N:6]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[C:5]2=[O:18])[CH2:3]1.[H-].[Na+].I[CH3:31].O>C1COCC1>[CH3:31][O:1][CH:2]1[C:27]2[C:19](=[CH:20][C:21]3[O:25][CH2:24][O:23][C:22]=3[CH:26]=2)[C:4]2([C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[N:6]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[C:5]2=[O:18])[CH2:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 59263478HCID 59263478, compound

Product 1

HCID 592635027-methoxy-1'-pentyl-6,7-dihydrospiro[indeno[5,6-d][1,3]dioxole-5,3'-indol]-2'(1H)-oneYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7-hydroxy-1′-pentyl-6,7-dihydrospiro[indeno[5,6-d][1,3]dioxole-5,3′-indol]-2′(1′H)-one (0.05 g, 0.14 mmol) in THF (10.0 mL) was added sodium hydride (0.01 mg, 0.21 mmol) at 0° C. The reaction mixture was stirred for half an hour followed by the addition of iodomethane (0.50 mL). The mixture was stirred at ambient temperature for two hours, then poured into water (100 mL), and extracted with ethyl acetate (100 mL). The organic layer was washed with water, dried over sodium sulfate and filtered. The filtrate was concentrated in vacuo to dryness. The residue was subjected to flash column chromatography to afford the title compound (0.03 g, 57%) as an oil: 1H NMR (300 MHz, CDCl3) δ 7.26-7.18 (m, 1H), 6.98-6.82 (m, 4H), 6.10 (s, 1H), 5.88 (s, 2H), 5.26 t, 1H), 3.88-3.63 (m, 2H), 3.45 (s, 3H), 2.71-2.54 (m, 2H), 1.80-1.65 (m, 2H), 1.45-1.29 (m, 4H), 0.90 (t, 3H); 13C NMR (75 MHz, CDCl3) δ 178.3, 148.9, 148.4, 142.4, 136.8, 136.6, 135.1, 128.1, 123.1, 122.6, 108.5, 105.0, 103.2, 101.5, 82.7, 57.9, 55.6, 43.4, 40.3, 29.1, 27.2, 22.4, 14.0: MS (ES+) m/z 402.4 (M+23).

Workup

  1. stirringThe mixture was stirred at ambient temperature for two hours
  2. extractionextracted with ethyl acetate (100 mL)
  3. washThe organic layer was washed with water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo to dryness

Sources & evidence

ORD record
ord-9e35181b0088446ba70f86674dc97031
Source dataset
uspto-grants-2012_01
Patent number
US08106087B2

Reaction notes

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