Formaldehyde → 4-(2-((2-methoxyethoxy)methoxy)ethoxy)-N-methylaniline

HRID 2274302Notes

Reaction equation

HRID 2274302 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:7][CH2:8][CH2:9][O:10][C:11]1[CH:17]=[CH:16][C:14]([NH2:15])=[CH:13][CH:12]=1.C=O.[BH-](OC(C)=O)(OC(C)=O)O[C:22](C)=O.[Na+].CCCCCC.C(OCC)(=O)C>O>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:7][CH2:8][CH2:9][O:10][C:11]1[CH:12]=[CH:13][C:14]([NH:15][CH3:22])=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 21226206Ethyl acetate hexaneHCID 867243654-(2-((2-Methoxyethoxy)methoxy)ethoxy)aniline

Product 1

HCID 867243694-(2-((2-methoxyethoxy)methoxy)ethoxy)-N-methylanilineYield 18.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 25 mL, 3-neck RBF equipped with a magnetic stirrer and calcium chloride guard tube, 4-(2-((2-methoxyethoxy)methoxy)ethoxy)aniline (1.0 g in 10 mL DMF) and formaldehyde (0.062 g) were added portion wise to the reaction mixture at 0° C. and stirred for an additional 10 minutes. NaBH(OAc)3 (0.88 g) was added and the mixture was stirred for 5 minutes. The reaction was monitored on TLC using hexane:ethyl acetate (5:5) as mobile phase. After completion of the reaction, the reaction mixture was poured in water and extracted with ethyl acetate. Organic layer was washed with brine, dried over sodium sulfate and concentrated completely under reduce pressure at 40° C. Crude material was purified by using column chromatography. Desired product was eluted with 7% ethyl acetate in hexane to give 0.200 g of 4-(2-((2-methoxyethoxy)methoxy)ethoxy)-N-methylaniline. M+1=256.0.

Workup

  1. customTo a 25 mL, 3-neck RBF equipped with a magnetic stirrer and calcium chloride guard tube
  2. stirringthe mixture was stirred for 5 minutes
  3. customAfter completion of the reaction
  4. extractionextracted with ethyl acetate
  5. washOrganic layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated completely
  8. customat 40° C
  9. customCrude material was purified
  10. washDesired product was eluted with 7% ethyl acetate in hexane

Sources & evidence

ORD record
ord-638493d51b3f4047b86b3f4aa91e1305
Source dataset
uspto-grants-2015_09
Patent number
US09126950B2

Reaction notes

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