Ethyl Acetoacetate → HCID 54092866, compound

HRID 974474Notes

Reaction equation

HRID 974474 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-0a753e8a1f5642b8ab8a29bfa5df25ff
Source dataset
uspto-grants-1991_11
Patent number
US05068346

Reaction notes

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