Methyl iodide → HCID 22349532, compound

HRID 896070Notes

Reaction equation

HRID 896070 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][CH:8]2[OH:11])=[CH:4][CH:3]=1.[H-].[Na+].I[CH3:15]>O1CCCC1>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][CH:8]2[O:11][CH3:15])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 27548246-bromo-2,3-dihydro-1H-inden-1-ol

Product 1

HCID 22349532HCID 22349532, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-bromoindanol (0.51 g, 2.4 mmol) in anhydrous tetrahydrofuran (10 mL), was added sodium hydride (0.097 g, 3.84 mmol) over a period of five minutes at room temperature. The reaction mixture was stirred at room temperature for fifteen minutes and iodomethane (0.22 mL, 3.6 mmol) was added. After thirty minutes at room temperature, the reaction mixture was partitioned between ethyl acetate (20 mL) and water (20 mL). The ethyl acetate layer was washed with brine (20 mL), dried over sodium sulfate and concentrated to yield the title compound (0.485 g, 89%). 1H NMR (CDCl3) : □ 7.5 (s, 1H), 7.3 (d, 1H), 7.0 (d, 1H), 4.7 (m, 1H), 3.3 (s, 3H), 3.0 (m, 1H), 2.7 (m, 1H), 2.3 (m, 1H), 2.0 (m, 1H).

Workup

  1. waitAfter thirty minutes at room temperature
  2. customthe reaction mixture was partitioned between ethyl acetate (20 mL) and water (20 mL)
  3. washThe ethyl acetate layer was washed with brine (20 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e819a17da0f845b0bfba26e925c8899f
Source dataset
uspto-grants-2005_07
Patent number
US06919335B2

Reaction notes

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