Tetrahydrofuran → 4-allyl-5-hydroxy-N-(4-fluorobenzyl)indole

HRID 342773Notes

Reaction equation

HRID 342773 reaction equation
[H-].[Na+].C([O:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]=[CH:10]2)C=C.[F:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21]Br)=[CH:19][CH:18]=1.O1C[CH2:28][CH2:27][CH2:26]1>>[CH2:28]([C:8]1[C:7]([OH:6])=[CH:15][CH:14]=[C:13]2[C:9]=1[CH:10]=[CH:11][N:12]2[CH2:21][C:20]1[CH:23]=[CH:24][C:17]([F:16])=[CH:18][CH:19]=1)[CH:27]=[CH2:26]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 680214-Fluorobenzyl bromideHCID 142392305-(prop-2-en-1-yloxy)-1H-indole

Product 1

HCID 539788064-allyl-5-hydroxy-N-(4-fluorobenzyl)indole

Procedure

To a solution of sodium hydride (60%, 140 mg, 3.47 mmol) in 4 mL tetrahydrofuran (THF) was added 5-allyloxyindole (Step A; 0.5 g, 2.89 mmol) in 1 mL and the mixture was stirred for 1 hour at ambient temperature. 4-fluorobenzyl bromide (0.43 mL, 3.32 mmol) was added and the reaction stirred 18 hours. The reaction was then quenched with saturated aqueous ammonium chloride and extracted with ethyl acetate. The organic layer was washed with water, brine, dried over magnesium sulfate, filtered through a short pad of silica and used directly in the next step.

Workup

  1. stirringthe reaction stirred 18 hours
  2. customThe reaction was then quenched with saturated aqueous ammonium chloride
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water, brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered through a short pad of silica

Sources & evidence

ORD record
ord-6a53ce4ab13b4ae6ace60c65c0114ee4
Source dataset
uspto-grants-1999_01
Patent number
US05859051

Reaction notes

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