Hydrochloric Acid → HCID 53685369, compound

HRID 1460326Notes

Reaction equation

HRID 1460326 reaction equation
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[H-].[Na+].C([Li])CCC.C(=O)=O.CC(C)=O.[F:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]([C:48]2[CH:53]=[CH:52][C:51]([F:54])=[CH:50][CH:49]=2)=[C:32]([N:37]2[C:41]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)=[N:40][N:39]=[N:38]2)[CH:33]=[CH:34][CH:35]=[O:36])=[CH:27][CH:26]=1.Cl.[NH4+].[Cl-]>O1CCCC1>[F:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]([C:48]2[CH:53]=[CH:52][C:51]([F:54])=[CH:50][CH:49]=2)=[C:32]([N:37]2[C:41]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)=[N:40][N:39]=[N:38]2)[CH:33]=[CH:34][CH:35]([OH:36])[CH2:5][C:3](=[O:4])[CH2:2][C:1]([O:7][CH2:8][CH3:9])=[O:6])=[CH:27][CH:26]=1

Participants

9

Reactant 7

HCID 313Hydrochloric AcidHCID 8868Ethyl Acetoacetate2×HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 18522661Acetone cardiceHCID 54453523HCID 54453523, compoundHCID 178418339Butyllithium

Product 1

HCID 53685369HCID 53685369, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

The dianion of ethyl acetoacetate was generated by adding 0.93 mL (7.3 mmoles) of purified ethyl acetoacetate to a suspension of 0.29 g (60% by weight in oil suspension, 7.3 mmoles) of sodium hydride in tetrahydrofuran (10 mL) at 0° C. under argon followed by the addition of 2.93 mL (7.3 mmoles) of 2.5 M n-butyllithium. The orange solution was stirred at 0° C. for one hour then cooled to -80° C. (dry ice-acetone). The dianion solution was added to a solution of 1.01 g (2.4 mmoles) of 5,5-bis(4-fluorophenyl)-4-(5-phenyl-1H-tetrazol-1-yl)-2,4-pentadienal in 20 mL of tetrahydrofuran at -80° C. under argon. After stirring for 10 minutes, the mixture was neutralized with 4 mL of 2 M HCl and 4 mL of saturated aqueous NH4Cl solution. The desired product was extracted with ethyl acetate and purified by silica gel column chromatography using a gradient elution of ethyl acetate-hexanes to yield 0.90 g (68%) of the title compound.

Workup

  1. stirringAfter stirring for 10 minutes
  2. extractionThe desired product was extracted with ethyl acetate
  3. custompurified by silica gel column chromatography
  4. washa gradient elution of ethyl acetate-hexanes

Sources & evidence

ORD record
ord-72ffa44e438c4067a86431dfb3bf9504
Source dataset
uspto-grants-1991_12
Patent number
US05070206

Reaction notes

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