Ethyl Acetoacetate → HCID 54092866, compound

HRID 330660Notes

Reaction equation

HRID 330660 reaction equation
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[F:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]([C:34]2[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=2)=[C:18]([C:23]2[N:27]([CH2:28][O:29][CH2:30][CH2:31][O:32][CH3:33])[N:26]=[N:25][N:24]=2)[CH:19]=[CH:20][CH:21]=[O:22])=[CH:13][CH:12]=1>O1CCCC1>[F:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]([C:34]2[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=2)=[C:18]([C:23]2[N:27]([CH2:28][O:29][CH2:30][CH2:31][O:32][CH3:33])[N:26]=[N:25][N:24]=2)[CH:19]=[CH:20][CH:21]([OH:22])[CH2:5][C:3](=[O:4])[CH2:2][C:1]([O:7][CH2:8][CH3:9])=[O:6])=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 8868Ethyl AcetoacetateHCID 53801859HCID 53801859, compound

Product 1

HCID 54092866HCID 54092866, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl acetoacetate dianion (2.6 mL of a freshly prepared 1M solution as described in Example 10) was added to a solution of 5,5-bis(4-fluorophenyl)-4-[1-(2-methoxyethoxy)methyl-1H-tetrazol-5-yl]-2,4-pentadienal (1.1 g, 2.6 mmoles) in 15 mL of tetrahydrofuran at -40° C. After stirring for 2 hours, analytical TLC eluted with 25% (v/v) ethyl acetate in hexane showed starting aldehyde and therefore, another 1.2 mL of dianion solution was added. The reaction mixture was allowed to warm to 0° C. and then quenched with 1N HCl. The mixture was extracted with methylene chloride, dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with 1% (v/v) methanol in methylene chloride to give 0.9 g of the title compound as an oil. MS (CI): m/e=557 for (M+H)+ ;

Workup

  1. washanalytical TLC eluted with 25% (v/v) ethyl acetate in hexane
  2. additionanother 1.2 mL of dianion solution was added
  3. customquenched with 1N HCl
  4. extractionThe mixture was extracted with methylene chloride
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography on silica gel eluting with 1% (v/v) methanol in methylene chloride

Sources & evidence

ORD record
ord-0bcce9bb36c74fc087f05c57b1401831
Source dataset
uspto-grants-1990_01
Patent number
US04897490

Reaction notes

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