Methyl iodide → Methyl 4-methyloxane-4-carboxylate

HRID 45058

Reaction equation

HRID 45058 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 1 N 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 1 N HCl (200 mL)
  5. extractionextracted with EtOAc
  6. customThe organic layer is dried
  7. customevaporated

Sources & evidence

ORD record
ord-65385f0298884ec392bf31a899d50845
Source dataset
uspto-grants-2013_09
Patent number
US08541432B2

Linked notes

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