Methyl iodide → HCID 117779445, compound

HRID 1527071Notes

Reaction equation

HRID 1527071 reaction equation
[CH3:1][C:2]([N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[C:7]1[CH3:15])([CH3:5])[CH2:3][OH:4].[H-].[Na+].I[CH3:19]>CN(C)C=O>[CH3:19][O:4][CH2:3][C:2]([N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[C:7]1[CH3:15])([CH3:1])[CH3:5]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 89740116HCID 89740116, compound

Product 1

HCID 117779445HCID 117779445, compoundYield 96.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-methyl-2-(2-methyl-1H-indol-1-yl)propan-1-ol (780 mg, 3.8 mmol) in anhydrous N,N-dimethylformamide (10 mL) was added sodium hydride (919 mg, 38.3 mmol) at 0° C. The resultant reaction mixture was allowed to stirred at 0° C. for 1 h. Iodomethane (5.4 g, 38.3 mmol) was added dropwise at 0° C., And then the resulting reaction mixture was allowed to stir for 3 hours at room temperature. The reaction mixture was quenched with water. The pH was adjusted to around 6 by progressively adding 2N hydro chloride below 0° C., extracted with acetic ester (50 mL×3). The combined organic phase was dried by anhydrous sodium sulphate, and then filtered. The filtrate was concentrated and purified by column chromatograph on silica gel eluted with (petrol ether/acetic ester 10:1→5:1) to give 1-(1-methoxy-2-methylpropan-2-yl)-2-methyl-1H-indole (800 mg, 96%) as a light yellow oil. LCMS (M+H+) m/z: calcd. 217.15. found 217.9.

Workup

  1. customThe resultant reaction mixture
  2. customthe resulting reaction mixture
  3. stirringto stir for 3 hours at room temperature
  4. customThe reaction mixture was quenched with water
  5. additionby progressively adding 2N hydro chloride below 0° C.
  6. extractionextracted with acetic ester (50 mL×3)
  7. dry with materialThe combined organic phase was dried by anhydrous sodium sulphate
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated
  10. custompurified by column chromatograph on silica gel
  11. washeluted with (petrol ether/acetic ester 10:1→5:1)

Sources & evidence

ORD record
ord-669709d24cab44ecbd0c7b020b96ce14
Source dataset
uspto-grants-2015_07
Patent number
US09085583B2

Reaction notes

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