Dimethylformamide diethylacetal → HCID 54507100, compound

HRID 1106559Notes

Reaction equation

[CH2:1]([C:3]1([CH2:16][CH3:17])[C:12]2[C:7](=[CH:8][C:9]([O:13][CH3:14])=[CH:10][CH:11]=2)[C:6](=[O:15])[CH2:5][CH2:4]1)[CH3:2].C(O[CH:21](OCC)[N:22]([CH3:24])[CH3:23])C>>[CH2:16]([C:3]1([CH2:1][CH3:2])[C:12]2[C:7](=[CH:8][C:9]([O:13][CH3:14])=[CH:10][CH:11]=2)[C:6](=[O:15])[C:5](=[CH:21][N:22]([CH3:24])[CH3:23])[CH2:4]1)[CH3:17]

Participants

Reactant 2

HCID 70913Dimethylformamide diethylacetal

HCID 18180234HCID 18180234, compound

Product 1

HCID 54507100HCID 54507100, compound

Procedure

4,4-Diethyl-3,4-dihydro-2-dimethylaminomethylene-7-methoxy-1(2H) naphthalenone was prepared from 4,4-diethyl-3,4-dihydro-7-methoxy-1(2H)naphthalenone (1.50 g, 6.5 mmol) and N,N-dimethylformamide diethyl acetal (3.3 ml, 19.5 mmol) to give the compound as a golden yellow oil (1.72 g) δH (CDCl3) 7.76 (1H, s), 7.63 (1H, d, J 2.9 Hz), 7.11 (1H, d, J 8.6 Hz), 6.96 (1H, dd, J 2.9, 8.6 Hz), 3.84 (3H, s), 3.13 (6H, s), 2.78 (2H, s), 1.66 (4H, q, J 7.5 Hz) and 0.77 (6H, t, J 7.4 Hz). MS (ES+) 288 (MH+, 100%).

Sources & evidence

ORD record: ord-d3848de6fa184a81975b473b62ae2bc4
Source dataset: uspto-grants-2000_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06057329

Reaction notes

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