Methyl iodide → HCID 67304947, compound

HRID 1009029Notes

Reaction equation

HRID 1009029 reaction equation
[CH3:1]C([O-])(C)C.[Na+].[CH3:7][C:8]1[S:9][CH:10]=[CH:11][C:12]=1[CH2:13][CH2:14][OH:15].CI>C1COCC1.CC(OC)(C)C>[CH3:1][O:15][CH2:14][CH2:13][C:12]1[CH:11]=[CH:10][S:9][C:8]=1[CH3:7]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 13144701HCID 13144701, compoundHCID 23676156Sodium t-butoxide

Product 1

HCID 67304947HCID 67304947, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

To a suspension of NaOtBu (3.00 g, 31.3 mmol) in THF (25 mL) was added the above prepared 2-(2-methyl-thiophen-3-yl)-ethanol (3.56 g, 25 mmol) and then methyl iodide (2.34 mL, 37.5 mmol). After stirring at rt for 1 h the reaction mixture was diluted with TBME (150 mL) and washed with 0.5M HCl (50 mL), 0.1M Na2S2O3 (50 mL) and 10% brine. The aqueous layers were extracted with TBME (50 mL) and the combined organic layers were dried (Na2SO4) and evaporated affording 3.78 g (96.7%, GC 96.0%) crude product as a yellow oil which was used without purification in the next step.

Workup

  1. additionwas added the
  2. washwashed with 0.5M HCl (50 mL), 0.1M Na2S2O3 (50 mL) and 10% brine
  3. extractionThe aqueous layers were extracted with TBME (50 mL)
  4. dry with materialthe combined organic layers were dried (Na2SO4)
  5. customevaporated
  6. customaffording 3.78 g (96.7%, GC 96.0%) crude product as a yellow oil which
  7. customwas used without purification in the next step

Sources & evidence

ORD record
ord-02312a0056df48178201375ed5b6e09c
Source dataset
uspto-grants-2011_07
Patent number
US07973051B2

Reaction notes

Loading…