Ethyl Acetoacetate → HCID 54396874, compound

HRID 1195359Notes

Reaction equation

HRID 1195359 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:24]=[N:25][N:26]([CH2:28][O:29][CH2:30][CH2:31][O:32][CH3:33])[N:27]=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:24]=[N:25][N:26]([CH2:28][O:29][CH2:30][CH2:31][O:32][CH3:33])[N:27]=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 54079002HCID 54079002, compound

Product 1

HCID 54396874HCID 54396874, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl acetoacetate dianion (2.1 mL of freshly prepared 1M solution as described in Example 10) was added to a solution of 5,5-bis(4-fluorophenyl)-4-[2-(2-methoxyethoxy)methyl-2H-tetrazol-5-yl]-2,4-pentadienal (0.9 g, 2.0 mmoles) in 15 mL of tetrahydrofuran at -50° C. After stirring for 1 hour, another 1 mL of dianion solution was added and the mixture stirred for an additional 30 minutes. The reaction mixture was quenched with 1N HCl and then extracted with methylene chloride. The organic extracts were 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 0.55 g of the title compound. MS (CI): m/e=557 for (M+H)+.

Workup

  1. additionanother 1 mL of dianion solution was added
  2. stirringthe mixture stirred for an additional 30 minutes
  3. customThe reaction mixture was quenched with 1N HCl
  4. extractionextracted with methylene chloride
  5. dry with materialThe organic extracts were dried (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-87854f92a0aa42c3b42801d44b19253e
Source dataset
uspto-grants-1992_05
Patent number
US05110940

Reaction notes

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