Methyl iodide → Methyl 2-methoxy-2-methylpropanoate

HRID 626525Notes

Reaction equation

HRID 626525 reaction equation
[OH:1][C:2]([CH3:8])([CH3:7])[C:3]([O:5][CH3:6])=[O:4].[H-].[Na+].I[CH3:12]>CN(C=O)C.CCOC(C)=O>[CH3:12][O:1][C:2]([CH3:8])([CH3:7])[C:3]([O:5][CH3:6])=[O:4]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 75024Methyl alpha-hydroxyisobutyrate

Product 1

HCID 12566213Methyl 2-methoxy-2-methylpropanoateYield 93%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A 0° C. solution of methyl 2-hydroxyisobutyrate (2 g, 16.93 mmol) in DMF (20 mL) was treated with NaH (60% in mineral oil, 0.813 g, 20.33 mmol), stirred for 0.5 h at 0° C., treated with iodomethane (1.269 mL, 20.29 mmol), allowed to warm to RT and stirred overnight. The mixture was diluted with EtOAc, quenched with cold satd. NH4Cl, extracted with EtOAc (3×) and the combined organics were washed with satd. NaHCO3, 10% LiCl, then brine, dried over Na2SO4 and concentrated to dryness to afford methyl 2-methoxy-2-methylpropanoate (2.08 g, 93%). 1H NMR (400 MHz, DMSO-d6): δ 3.64 (s, 3H), 3.11 (s, 3H), 1.30 (s, 6H).

Workup

  1. temperatureto warm to RT
  2. stirringstirred overnight
  3. customquenched with cold satd
  4. extractionNH4Cl, extracted with EtOAc (3×)
  5. washthe combined organics were washed with satd
  6. dry with materialNaHCO3, 10% LiCl, then brine, dried over Na2SO4
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-afed73f2967c43c6bb31c18c11d3d7d1
Source dataset
uspto-grants-2016_04
Patent number
US09309224B2

Reaction notes

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