Formaldehyde → (E)-2-(2-(2-(2-Hydroxyethoxy)ethoxy)ethoxy)-5-(4-dimethylaminostyryl)pyridine

HRID 1890157Notes

Reaction equation

HRID 1890157 reaction equation
[C:1]([BH3-])#[N:2].[Na+].[OH:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18](/[CH:21]=[CH:22]/[C:23]2[CH:28]=[CH:27][C:26](N)=[CH:25][CH:24]=2)=[CH:17][N:16]=1.C=O.[C:32](=O)(O)[O-].[Na+]>C(O)(=O)C>[OH:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18](/[CH:21]=[CH:22]/[C:23]2[CH:28]=[CH:27][C:26]([N:2]([CH3:1])[CH3:32])=[CH:25][CH:24]=2)=[CH:17][N:16]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 67384250HCID 67384250, compound

Product 1

HCID 67384227(E)-2-(2-(2-(2-Hydroxyethoxy)ethoxy)ethoxy)-5-(4-dimethylaminostyryl)pyridineYield 95%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Sodium cyanoborohydride (36 mg, 0.57 mmol) was added to a solution of compound 8 (65 mg, 0.19 mmol) and paraformaldehyde (57 mg, 1.9 mmol) in acetic acid (10 ml). The reaction mixture was stirred at room temperature overnight and poured onto ice. Sodium bicarbonate was used to adjust pH to 9. Reaction mixture was extracted with ethyl acetate. Organic layer was separated, washed with brine, dried over anhydrous sodium sulfate and evaporated. The residue was purified with PTLC (5% MeOH in DCM as the developing solvent) to give product 9 (67 mg, Yield: 95%): 1H NMR (200 MHz, CDCl3): δ.8.14 (1H, d, J=2.4 Hz), 7.76 (1H, d, d, J1=8.6 Hz, J2=2.4 Hz), 7.39 (2H, d, J=8.8 Hz), 6.87 (2H, m), 6.76 (3H, m), 4.50 (2H, t, J=4.8 Hz), 3.87 (2H, t, J=4.8 Hz), 3.70 (6H, m), 3.61 (2H, m), 2.98 (6H, s), 2.49 (1H, b), HRMS (EI) m/z calcd. for [C21H28N2O4]+ 372.2049.

Workup

  1. additionpoured onto ice
  2. customReaction mixture
  3. extractionwas extracted with ethyl acetate
  4. customOrganic layer was separated
  5. washwashed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated
  8. customThe residue was purified with PTLC (5% MeOH in DCM as the developing solvent)

Sources & evidence

ORD record
ord-3322dd51566e4439a6b2558edec583b9
Source dataset
uspto-grants-2013_08
Patent number
US08506929B2

Reaction notes

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