Formaldehyde → HCID 118098780, compound

HRID 708914Notes

Reaction equation

HRID 708914 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:25][C:26]#[N:27])=[C:13]([CH:24]=1)[CH2:14][N:15]([CH3:23])[C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:28](=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]([NH:8][C:9]1[CH:10]=[CH:11][C:12]([C:25]([C:26]#[N:27])=[CH2:28])=[C:13]([CH:24]=1)[CH2:14][N:15]([CH3:23])[C:16](=[O:22])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[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 118098779HCID 118098779, compound

Product 1

HCID 118098780HCID 118098780, compoundYield 79%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

36E (0.344 g, 0.916 mmol) was dissolved in toluene (4 mL), and to the resulting solution were sequentially added potassium carbonate (0.253 g, 1.832 mmol), paraformaldehyde (0.275 g, 9.16 mmol) and tris(3,6-dioxaheptyl)amine (tda-1) (0.029 mL, 0.092 mmol). The reaction mixture was stirred at 85° C. for 10 h, then 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 by flash chromatography (0-40% EtOAc/hexanes) to give 36F (0.280 g, 0.723 mmol, 79% yield) as a colorless syrup, which solidified upon standing. MS (ESI) m/z: 388.3 [M+1]+. 1H NMR: (400 MHz, CDCl3) δ ppm 7.48 (1H, d, J=16.56 Hz), 7.20 (1H, d, J=8.28 Hz), 7.05-7.16 (1H, m), 6.63 (1H, br. s.), 6.22 (1H, s), 5.91 (1H, s), 4.55 (2H, s), 2.82 (3H, br. s.), 1.38-1.57 (18H, m).

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 by flash chromatography (0-40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-a342e50d30604aab89e3a18de6efe670
Source dataset
uspto-grants-2015_11
Patent number
US09174974B2

Reaction notes

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