Acrolein dimethyl acetal → 4-[4-(5-Dimethoxymethyl-4,5-dihydro-isoxazol-3-yl)-phenoxymethyl]-2-methyl-quinoline

HRID 1245392

Reaction equation

HRID 1245392 reaction equation
[CH3:1][O:2][CH:3]([O:6][CH3:7])[CH:4]=[CH2:5].[CH3:8][C:9]1[CH:18]=[C:17]([CH2:19][O:20][C:21]2[CH:29]=[CH:28][C:24]([CH:25]=[N:26][OH:27])=[CH:23][CH:22]=2)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=1>>[CH3:1][O:2][CH:3]([O:6][CH3:7])[CH:4]1[O:27][N:26]=[C:25]([C:24]2[CH:23]=[CH:22][C:21]([O:20][CH2:19][C:17]3[C:16]4[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=4)[N:10]=[C:9]([CH3:8])[CH:18]=3)=[CH:29][CH:28]=2)[CH2:5]1

Participants

3

Reactant 2

HCID 80145Acrolein dimethyl acetalHCID 738530794-(2-Methyl-quinolin-4-ylmethoxy)-benzaldehyde oxime

Product 1

HCID 219111774-[4-(5-Dimethoxymethyl-4,5-dihydro-isoxazol-3-yl)-phenoxymethyl]-2-methyl-quinolineYield 100%

Procedure

Following a procedure analogous to that used in Example step 1c, but using 3,3-dimethoxy-propene and 4-(2-methyl-quinolin-4-ylmethoxy)-benzaldehyde oxime from step 1b, the crude reaction was partitioned between ethyl acetate and water and the organic layer was washed with brine, dried over magnesium sulfate, and concentrated to give 4-[4-(5-dimethoxymethyl-4,5-dihydro-isoxazol-3-yl)-phenoxymethyl]-2-methyl-quinoline (0.4 g, 100%) as a crude oil. MS found: (M+H)+=393.

Workup

  1. customthe crude reaction
  2. customwas partitioned between ethyl acetate and water
  3. washthe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4924a64531f34706a08014fded8fd5f9
Source dataset
uspto-grants-2006_10
Patent number
US07125870B2

Linked notes

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