Methyl iodide → Methyl 4-methyloxane-4-carboxylate

HRID 453127Notes

Reaction equation

HRID 453127 reaction equation
[CH:1](NC(C)C)(C)C.[Li]CCCC.[O:13]1[CH2:18][CH2:17][CH:16]([C:19]([O:21][CH3:22])=[O:20])[CH2:15][CH2:14]1.IC>C1COCC1>[CH3:22][O:21][C:19]([C:16]1([CH3:1])[CH2:17][CH2:18][O:13][CH2:14][CH2:15]1)=[O:20]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 7912DiisopropylamineHCID 27735202H-Pyran-4-carboxylic acid, tetrahydro-, methyl esterHCID 178418339Butyllithium

Product 1

HCID 11019135Methyl 4-methyloxane-4-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of diisopropylamine (10.2 ml, 72.8 mmol) in THF (400 ml) at −78° C., n-BuLi (25.2 ml, 1.6 M in heptane) is added. The reaction is removed from the bath and stirred for 10 min. It is then cooled to −78° C. again and methyl tetrahydro-2H-pyran-4-carboxylate (6.48 ml, 48.6 mmol) is added. After 30 min, iodomethane (6.07 ml, 97 mmol) is added and the reaction allowed to reach rt. The reaction is then quenched with 1N HCl (200 mL) and extracted with EtOAc. The organic layer is dried and evaporated to give 4-methyl-tetrahydro-pyran-4-carboxylic acid methyl ester. MS (ESI) m/z 159.3 (M+1).

Workup

  1. customThe reaction is removed from the bath
  2. waitAfter 30 min
  3. customto reach rt
  4. customThe reaction is then quenched with 1N HCl (200 mL)
  5. extractionextracted with EtOAc
  6. customThe organic layer is dried
  7. customevaporated

Sources & evidence

ORD record
ord-0ea68789dc9c4eb98973f81b3e4a3421
Source dataset
uspto-grants-2013_07
Patent number
US08492393B2

Reaction notes

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