Dimethylformamide dimethyl acetal → 3-Dimethylamino-2-(2-methoxyphenyl)propenal

HRID 1581806Notes

Reaction equation

HRID 1581806 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][CH2:10][OH:11].[CH3:12][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH2:20][CH:21]=[O:22].CO[CH:25](OC)[N:26]([CH3:28])[CH3:27]>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][CH:10]=[O:11].[CH3:25][N:26]([CH3:28])[CH:27]=[C:20]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[O:13][CH3:12])[CH:21]=[O:22]

Participants

5

Reactant 3

HCID 78373Dimethylformamide dimethyl acetalHCID 819092-Methoxyphenethyl alcoholHCID 2695482-(2-Methoxyphenyl)acetaldehyde

Product 2

HCID 2695482-(2-Methoxyphenyl)acetaldehydeHCID 865899133-Dimethylamino-2-(2-methoxyphenyl)propenalYield 90%

Procedure

(2-Methoxyphenyl)acetaldehyde is prepared by oxidation of 2-(2-methoxyphenyl)ethanol according to the procedure disclosed in J. Org. Chem., 49:1720, 1999. A mixture of (2-methoxyphenyl)acetaldehyde (3.8 g, 25.3 mmol) and dimethylformamide dimethyl acetal (4.52 g, 37.9 mmol) is stirred at room temperature for 1 hour. Excess of the acetal is removed under reduced pressure to leave 4.68 g of 3-dimethylamino-2-(2-methoxyphenyl)propenal (90%).

Workup

  1. customExcess of the acetal is removed under reduced pressure

Sources & evidence

ORD record
ord-b8268a6c788a4d04ad8f2aa6685f2fc2
Source dataset
uspto-grants-2004_05
Patent number
US06730792B2

Reaction notes

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