Diethylene Glycol Monomethyl Ether → HCID 67508105, compound

HRID 1770754Notes

Reaction equation

HRID 1770754 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][OH:8].[H-].[Na+].I[CH2:12][CH2:13][CH2:14][N:15]1[C:19](=[O:20])[C:18]([CH3:22])([CH3:21])[NH:17][C:16]1([CH3:24])[CH3:23]>CN(C)C=O>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:12][CH2:13][CH2:14][N:15]1[C:19](=[O:20])[C:18]([CH3:22])([CH3:21])[NH:17][C:16]1([CH3:23])[CH3:24]

Participants

5

Reactant 3

HCID 8134Diethylene Glycol Monomethyl EtherHCID 24758Sodium hydrideHCID 67508188HCID 67508188, compound

Product 1

HCID 67508105HCID 67508105, compoundYield 8.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Neat diethylene glycol monomethyl ether (1.30 mL, 11.0 mmol, 1.5 equiv.) was added dropwise to a suspension of sodium hydride (400 mg, 60% disp., 10 mmol, 1.35 equiv.) in N,N-dimethylformamide (10 mL) over 5 minutes. The mixture was stirred at room temperature for 15 minutes, before a solution of 3-(3-iodopropyl)-2,2,5,5-tetramethylimidazolidin-4-one (2.29 g, 7.38 mmol) in N,N-dimethylformamide (10 mL) was added via cannula over 15 minutes. The mixture was then stirred overnight at room temperature. After 23 hours, the mixture was concentrated to a yellow oil which was absorbed on silica (5 g). Chromatography on silica (0-6% methanol in dichloromethane) afforded the title compound (190 mg, 8.5%) as a pale yellow oil. 1H NMR (400 MHz, CDCl3) δ 3.68-3.64 (m, 4H), 3.63-3.59 (m, 2H), 3.57-3.54 (m, 2H), 3.53 (t, J=6.1 Hz, 2H), 3.39 (s, 3H), 3.29-3.24 (m, 2H), 1.96-1.89 (m, 2H), 1.82 (br s, 1H), 1.41 (s, 6H), 1.32 (s, 6H); LRMS (ESI/APCI) m/z 303 [M+H]+.

Workup

  1. additionwas added via cannula over 15 minutes
  2. waitAfter 23 hours
  3. concentrationthe mixture was concentrated to a yellow oil which
  4. customwas absorbed on silica (5 g)

Sources & evidence

ORD record
ord-cda68f7f3cd345d082e2c4a03f1b8313
Source dataset
uspto-grants-2016_02
Patent number
US09248117B2

Reaction notes

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