2-(Dimethylamino)ethanol → 3-[2-(Dimethylamino)ethoxy]-4-methoxybenzaldehyde

HRID 401216Notes

Reaction equation

HRID 401216 reaction equation
[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][OH:5].C(N(CC)CC)C.CS(Cl)(=O)=O.O[C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][C:27]=1[O:28][CH3:29])[CH:23]=[O:24].C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl.CCOC(C)=O>[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][O:5][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][C:27]=1[O:28][CH3:29])[CH:23]=[O:24]

Participants

8

Reactant 5

HCID 79022-(Dimethylamino)ethanolHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 12127IsovanillinHCID 31297Methanesulfonyl chloride

Product 1

HCID 209862903-[2-(Dimethylamino)ethoxy]-4-methoxybenzaldehydeYield 31.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-(dimethylamino)ethanol (5.0 g, 56.0 mmol) and triethylamine (8.5 g, 84.0 mmol) in anhydrous DCM (50 mL) was added methanesulfonyl chloride (7.1 g, 62.0 mmol) at 0° C. under N2. The mixture was stirred at 0° C. for 1 hour. The solvent was removed in vacuo (6.0 g, yield 65%), and the crude was taken up in CH3CN (100 mL). 3-hydroxy-4-methoxybenzaldehyde (5.5 g, 36.0 mmol) and potassium carbonate (13.8 g, 100.0 mol) was added and reaction was refluxed under N2 overnight. An aqueous/EtOAc workup was followed, and crude was purified by silica gel column chromatography (PE:EtOAc=3:1) to give product (2.5 g, yield 31%) as yellow solid.

Workup

  1. customThe solvent was removed in vacuo (6.0 g, yield 65%)
  2. customreaction
  3. temperaturewas refluxed under N2 overnight
  4. customcrude was purified by silica gel column chromatography (PE:EtOAc=3:1)

Sources & evidence

ORD record
ord-eb3c14e81e5947d6a152e237538b9718
Source dataset
uspto-grants-2014_06
Patent number
US08741915B2

Reaction notes

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