Sodium Methoxide → 7,7-Dimethyl-3-oxa-6-azaoctan-1-ol

HRID 2113250Notes

Reaction equation

HRID 2113250 reaction equation
C([O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][NH:10][C:11]([CH3:14])([CH3:13])[CH3:12])(=O)C.C[O-].[Na+]>CO>[C:11]([NH:10][CH2:9][CH2:8][O:7][CH2:6][CH2:5][OH:4])([CH3:14])([CH3:13])[CH3:12]

Participants

4

Reactant 2

HCID 10942334Sodium Methoxide2×HCID 86616350HCID 86616350, compound

Product 1

HCID 136436647,7-Dimethyl-3-oxa-6-azaoctan-1-olYield 70%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-(2-t-Butylaminoethoxy)ethyl acetate (1.2 g, 5.9 mmol) was stirred for 7 hours with sodium methoxide (0.015 g, 0.28 mmol) in methanol (15 mL) at room temperature. The NMR analysis of the reaction mixture showed approximately 20% conversion. Additional sodium methoxide (0.015 g, 0.28 mmol) was added to the reaction mixture and it was stirred for an additional 3 hours. Solvent was evaporated and the liquid phase was separated from the solid by filtration. The solid was washed with diethyl ether. The combined filtrates were evaporated under reduced pressure to remove a solvent to give 2-(2-t-butylamino-ethoxy)ethanol (EETB) as yellowish liquid (0.65 g, 70%) 1H NMR δ 1.12 (s, 9H), 2.76 (t, J=5.1 Hz, 2H), 3.59-3.66 (m, 4H), 3.70-3.73 (m, 2H); 13C NMR δ 28.8, 42.2, 50.3, 61.8, 71.3, 72.6.

Workup

  1. customSolvent was evaporated
  2. customthe liquid phase was separated from the solid by filtration
  3. washThe solid was washed with diethyl ether
  4. customThe combined filtrates were evaporated under reduced pressure
  5. customto remove a solvent

Sources & evidence

ORD record
ord-b2516ed036e64fc8b0f7e24a627f238f
Source dataset
uspto-grants-2009_04
Patent number
US07524990B2

Reaction notes

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