Formaldehyde → HCID 118098727, compound

HRID 708852Notes

Reaction equation

HRID 708852 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:10][C:11]1[CH:16]=[C:15]([NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH:14]=[CH:13][C:12]=1[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH3:9])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:31](=O)([O-])[O-].[K+].[K+].C=O.C(N(CCOCCOC)CCOCCOC)COCCOC>C1(C)C=CC=CC=1.CCOC(C)=O.O>[C:1]([O:5][C:6]([N:8]([CH2:10][C:11]1[CH:16]=[C:15]([NH:17][C:18]([O:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[O:19])[CH:14]=[CH:13][C:12]=1[C:25](=[CH2:31])[C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH3:9])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 4

HCID 712FormaldehydeHCID 11430Potassium CarbonateHCID 112414Ethanamine, 2-(2-methoxyethoxy)-N,N-bis[2-(2-methoxyethoxy)ethyl]-HCID 118093006HCID 118093006, compound

Product 1

HCID 118098727HCID 118098727, compoundYield 31.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

15D (0.573 g, 1.356 mmol) was dissolved in toluene (5 mL), and to the resulting solution were sequentially added potassium carbonate (0.375 g, 2.71 mmol), paraformaldehyde (0.407 g, 13.56 mmol) and tris(3,6-dioxaheptyl)amine (tda-1) (0.043 mL, 0.136 mmol). The reaction mixture was stirred at 85° C. for 10 h. The reaction mixture was diluted with EtOAc (20 mL) and water (10 mL) and stirred for 15 min. The organic phase was separated, washed with water (3×10 mL), brine (1×10 mL) and dried (Na2SO4). EtOAc was removed under reduced pressure and the residue was purified flash chromatography (0-35% EtOAc/hexanes). Fractions were combined and concentrated under reduced pressure to give 15E (0.187 g, 31.7% yield) as a colorless syrup. MS (ESI) m/z: 435.1 [M+1]+. 1H NMR: (400 MHz, CDCl3) δ ppm 7.40 (1H, d, J=5.77 Hz), 7.06 (2H, d, J=8.28 Hz), 6.50 (1H, s), 5.67 (1H, d, J=1.76 Hz), 4.27-4.39 (2H, m), 4.21 (2H, q, J=7.03 Hz), 2.61-2.77 (3H, m), 1.38-1.55 (18H, m), 1.26 (3H, t, J=7.03 Hz).

Workup

  1. stirringstirred for 15 min
  2. customThe organic phase was separated
  3. washwashed with water (3×10 mL), brine (1×10 mL)
  4. dry with materialdried (Na2SO4)
  5. customEtOAc was removed under reduced pressure
  6. customthe residue was purified flash chromatography (0-35% EtOAc/hexanes)
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1d02de1f441e41be9c85a1bee48287a4
Source dataset
uspto-grants-2015_11
Patent number
US09174974B2

Reaction notes

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