Dimethylformamide diethylacetal → HCID 54342294, compound

HRID 1359006Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]([CH3:14])[CH2:8][CH2:9][C:10]2=[O:13])=[CH:5][CH:4]=1.C(O[CH:18](OCC)[N:19]([CH3:21])[CH3:20])C>>[CH3:18][N:19]([CH:21]=[C:9]1[CH2:8][CH:7]([CH3:14])[C:6]2[C:11](=[CH:12][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[C:10]1=[O:13])[CH3:20]

Participants

Reactant 2

HCID 70913Dimethylformamide diethylacetal

HCID 15677800HCID 15677800, compound

Product 1

HCID 54342294HCID 54342294, compoundYield 75%

Procedure

The 3,4-dihydro-2-dimethylaminomethylene-7-methoxy-4-methyl-1(2H)-naphthalenone starting material was prepared from 3,4-dihydro-7-methoxy-4-methyl-1-(2H) naphthalenone (950 mg, 5.0 mmol) [Gupta, A S; et al Tetrahedron (1967), 23, 2481], and N,N-dimethylformamide diethyl acetal (2.6 ml, 15.0 mmol). The product was purified by chromatography on silica (70% ethyl acetate in hexane—ethyl acetate) to give 3,4-dihydro-2-dimethylaminomethylene-7-methoxy-4-methyl-1(2H) naphthalenone as a yellow oil (920 mg). δH (CDCl3) 7.77 (1H, s), 7.58 (1H, d, J 2.9 Hz), 7.12 (1H, d, J 8.4 Hz), 6.97 (1H, dd, J 2.9, 8.4 Hz), 3.85 (3H, s), 3.13 (6H, s), 3.01-2.90 (2H, m), 2.76-2.70 (1H, m) and 1.28 (3H, d, J 6.9 Hz). IR (liquid film) 1647 (s), 1547 (s) cm−1.

Workup

customThe product was purified by chromatography on silica (70% ethyl acetate in hexane—ethyl acetate)

Sources & evidence

ORD record: ord-b08b4a42ee35411ebcd1b74cd14ee17f
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06599908B1

Reaction notes

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