Methyl iodide → 2-Methoxymethyl-3-methyl-thiophene

HRID 252273

Reaction equation

HRID 252273 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:8]=[CH:7][S:6][C:5]=1[CH2:9][OH:10].I[CH3:12]>O1CCCC1>[CH3:12][O:10][CH2:9][C:5]1[S:6][CH:7]=[CH:8][C:4]=1[CH3:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 12875263(3-Methylthiophen-2-yl)methanol

Product 1

HCID 668575872-Methoxymethyl-3-methyl-thiopheneYield 87.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Sodium hydride (2.2 g ˜60%, 55.2 mmol, 1.2 equiv.) was suspended in dry tetrahydrofuran under an inert atmosphere. At 5° C. a solution of (3-methyl-thiophen-2-yl)-methanol (5.16 g, 46 mmol) in dry tetrahydrofuran was added dropwise. The mixture was stirred at room temp. for 1 hour, then iodomethane (7.8 g, 55.2 mmol, 1.2 equiv.) was added dropwise. The mixture was stirred overnight at room temp. and then quenched with diluted acid and extracted with diethyl ether. The combined organic extracts were washed with brine, dried over magnesiumsulfat dihydrate, filtered and evaporated to give 5.7 g of the title compound as a light green oil. GC-MS (EI) M=142.

Workup

  1. stirringThe mixture was stirred overnight at room temp.
  2. customquenched
  3. additionwith diluted acid
  4. extractionextracted with diethyl ether
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over magnesiumsulfat dihydrate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-641187dfe270423d8c1e0a77be545351
Source dataset
uspto-grants-2011_01
Patent number
US07868030B2

Linked notes

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