4-Hydroxybenzaldehyde → 4-(2-pyrrolidin-1-ylethoxy)benzaldehyde

HRID 2368889Notes

Reaction equation

HRID 2368889 reaction equation
Cl[CH2:2][CH2:3][N:4]1[CH2:8][CH2:7][CH2:6][CH2:5]1.[OH:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]=[O:15])=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[N:4]1([CH2:3][CH2:2][O:9][C:10]2[CH:17]=[CH:16][C:13]([CH:14]=[O:15])=[CH:12][CH:11]=2)[CH2:8][CH2:7][CH2:6][CH2:5]1

Participants

6

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 816691-(2-Chloroethyl)pyrrolidine

Product 1

HCID 9768444-(2-pyrrolidin-1-ylethoxy)benzaldehydeYield 54.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 1-(2-chloroethyl)pyrrolidine (1.19 g, 8.83 mmol), 4-hydroxybenzaldehyde (1.02 g, 8.33 mmol), and potassium carbonate (2.30 g, 16.7 mmol) in DMF (5 mL) was heated at 60° C. overnight. The reaction mixture was diluted with H2O and extracted with ethyl acetate (2×50 mL). The combined organic extracts were washed (50 mL brine), dried over Na2SO4, and concentrated. The crude material was purified on a silica gel column to yield 4-(2-(pyrrolidin-1-yl)ethoxy)benzaldehyde (996 mg, 53%). 1H NMR (CDCl3): δ 9.90 (s, 1H), 7.85 (d, 2H), 7.03 (d, 2H), 4.22 (t, 2H), 2.96 (t, 2H), 2.69 (m, 4H), 1.82 (m, 4H).

Workup

  1. extractionextracted with ethyl acetate (2×50 mL)
  2. washThe combined organic extracts were washed (50 mL brine)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude material was purified on a silica gel column

Sources & evidence

ORD record
ord-e11a9e6286784c159da821bc24b165e7
Source dataset
uspto-grants-2014_04
Patent number
US08703810B2

Reaction notes

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