Methyl iodide → HCID 57936246, compound

HRID 1434913Notes

Reaction equation

HRID 1434913 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][CH2:8][CH2:9][OH:10].[H-].[Na+].I[CH3:14]>C1COCC1.O>[CH3:14][O:10][CH2:9][CH2:8][CH2:7][CH2:6][C:2]1[S:1][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 126238624-(Thiophen-2-yl)butan-1-ol

Product 1

HCID 57936246HCID 57936246, compound

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

A solution of 4-thiophen-2-yl-butan-1-ol (4.55 g, 29.09 mmol) in 20 ml of THF was carefully added to a stirred suspension of oil-free sodium hydride (1.05 g, 43.75 mmol) in 15 ml of THF. When the addition was complete, the mixture was heated to 50° C. and stirring continued for 1 hour. Iodomethane (2.7 ml, 43.75 mmol) was then added and the turbid solution was stirred at 50° C. for another 2 hours. After cooling, a few drops of water were added and the mixture was partitioned between 1N-HCl and ether. The organic layer was washed with saturated sodium bicarbonate solution and brine. Drying over sodium sulfate and careful evaporation (product is volatile) gave a pale yellow oil. Yield: 4.45 g (90%).

Workup

  1. additionWhen the addition
  2. stirringthe turbid solution was stirred at 50° C. for another 2 hours
  3. temperatureAfter cooling
  4. customthe mixture was partitioned between 1N-HCl and ether
  5. washThe organic layer was washed with saturated sodium bicarbonate solution and brine
  6. dry with materialDrying over sodium sulfate and careful evaporation (product is volatile)
  7. customgave a pale yellow oil

Sources & evidence

ORD record
ord-eb1b806ff2da40a4b56a946a1ca4317a
Source dataset
uspto-grants-2009_11
Patent number
US07615562B2

Reaction notes

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