Methyl iodide → HCID 23590029, compound

HRID 898442Notes

Reaction equation

HRID 898442 reaction equation
[CH2:1]([O:3][C:4](=[O:31])[C:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][C:18]2[N:19]=[C:20]([C:24]3[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=3)[O:21][C:22]=2[CH3:23])=[CH:11][CH:10]=1)([CH3:7])[CH3:6])[CH3:2].[CH3:32]I.[OH-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:31])[C:5]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][CH2:16][CH2:17][C:18]2[N:19]=[C:20]([C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:32])=[CH:26][CH:25]=3)[O:21][C:22]=2[CH3:23])=[CH:13][CH:14]=1)([CH3:7])[CH3:6])[CH3:2]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 135617795HCID 135617795, compound

Product 1

HCID 23590029HCID 23590029, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 2-(4-{2-[2-(4-hydroxy-phenyl)-5-methyl-oxazol-4-yl]-ethoxy}-phenoxy)-2-methyl-propionic acid ethyl ester (0.15 g, 0.352 mmol), methyl iodide (0.15 g, 1.06 mmol), tetrabutylammonium bromide (0.023 g, 0.0713) mmol) in CH2Cl2 (8 mL) was treated with a 50% weight solution of NaOH (0.1 mL), and stirred at room temperature. The reaction mixture was extracted with water and more CH2Cl2 and the organic layer dried (MgSO4). The solvent was removed in vacuo to give a crude oil which was purified by flash chromatography (2/1 hexanes/EtOAc) to afford 0.038 g (25%) 2-(4-{2-[2-(4-methoxy-phenyl)-5-methyl-oxazol-4-yl]-ethoxy}-phenoxy)-2-methyl-propionic acid ethyl ester. 1H NMR (500 MHz, CDCl3) δ 7.87-7.85 (m, 2), 6.90-6.88 (m, 2H), 6.78-6.71 (m, 4H), 4.21-4.06 (m, 4H), 3.80 (s, 3H), 2.88 (t, 2H, J=6.60 Hz), 2.29 (s, 3H), 1.47 (s, 6H), 1.23 (t, 3H, J=7.33 Hz); MS (ES+) Calc'd for C25H30NO6: Found m/e 440 (M+1, 100%).

Workup

  1. extractionThe reaction mixture was extracted with water and more CH2Cl2
  2. dry with materialthe organic layer dried (MgSO4)
  3. customThe solvent was removed in vacuo
  4. customto give a crude oil which
  5. customwas purified by flash chromatography (2/1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-f4f593f9e7b14a5187824c2f6406d69d
Source dataset
uspto-grants-2008_04
Patent number
US07351728B2

Reaction notes

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