Methyl iodide → HCID 68912696, compound

HRID 1887538Notes

Reaction equation

HRID 1887538 reaction equation
C(O[C:6]1[CH:14]=C[C:9]([C:10]([OH:12])=[O:11])=[CH:8][CH:7]=1)CCC.CN(C)[CH2:17][CH2:18]N(C)C.[CH:23]([Li])([CH2:25][CH3:26])[CH3:24].CI.C1C[O:33]CC1>O>[CH2:24]([O:33][C:14]1[C:17]([CH3:18])=[C:9]([CH:8]=[CH:7][CH:6]=1)[C:10]([OH:12])=[O:11])[CH2:23][CH2:25][CH3:26]

Participants

7

Reactant 5

HCID 6328Methyl iodideHCID 8028Tetrahydrofuran2×HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 729714-Butoxybenzoic acidHCID 178418400CID 53628100

Product 1

HCID 68912696HCID 68912696, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
-90 °C

Procedure

A mixture of 4-butoxybenzoic acid (10 g), N,N,N′,N′-tetramethylethylenediamine (13.2 g) and THF (75 mL) was cooled to −90° C., and sec-butyllithium (81 mL; 1.4 M in hexane) was added over the course of 30 minutes. After a further 30 minutes, the mixture was warmed to −78° C., and a solution of methyl iodide (12.8 mL) in THF (10 mL) was added dropwise. The reaction solution was allowed to warm to room temperature and the mixture was hydrolyzed with water and extracted with ethyl acetate. The organic phase was dried over magnesium sulfate and concentrated. The residue was purified by chromatography on silica gel. The product with the molecular weight of 208.26 (C12H16O3) was obtained in this way; MS (ESI): 209 (M+H+).

Workup

  1. temperaturethe mixture was warmed to −78° C.
  2. temperatureto warm to room temperature
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography on silica gel
  7. customThe product with the molecular weight of 208.26 (C12H16O3) was obtained in this way

Sources & evidence

ORD record
ord-6c7de6950d3e4811896a8fe2d3fa2259
Source dataset
uspto-grants-2013_08
Patent number
US08501771B2

Reaction notes

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