Methyl acetoacetate → HCID 86746566, compound

HRID 2082338Notes

Reaction equation

HRID 2082338 reaction equation
[C:1]([O:7][CH3:8])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[H-].[Na+].C([Li])CCC.[F:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[N:24]([CH2:38][CH2:39][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[C:25](=[O:37])[C:26]3[C:31]([C:32]=2/[CH:33]=[CH:34]/[CH:35]=[O:36])=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:19][CH:18]=1.[Cl-].[NH4+]>O1CCCC1.CCCCCC>[F:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[N:24]([CH2:38][CH2:39][C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=3)[C:25](=[O:37])[C:26]3[C:31]([C:32]=2/[CH:33]=[CH:34]/[CH:35]([OH:36])[CH2:5][C:3](=[O:4])[CH2:2][C:1]([O:7][CH3:8])=[O:6])=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:19][CH:18]=1

Participants

8

Reactant 5

HCID 7757Methyl acetoacetateHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 19778191HCID 19778191, compoundHCID 178418339Butyllithium

Product 1

HCID 86746566HCID 86746566, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

In an atmosphere of argon gas, methyl acetoacetate (0.29 ml) was added to a suspension of sodium hydride (60%, in oil) (129 mg) in anhydrous tetrahydrofuran (15 ml) at 0° C. under stirring, followed by stirring for 10 minutes. After cooling at -78° C., the mixture to which a solution of n-butyllithium in n-hexane (1.6M, 2.7 ml) was added was stirred for 10 minutes. A solution of the compound (748 mg) obtained by Step 2 of Reference Example 13 in anhydrous tetrahydrofuran (7 ml) was added to the mixture, followed by stirring at -78° C. for 30 minutes. The reaction mixture to which aqueous ammonium chloride solution was added was extracted with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate and distilled to remove the solvent. The residue was subjected to a silica gel column chromatography using ethyl acetate-n-hexane to give the title compound (768 mg) as pale yellow oily substance.

Workup

  1. stirringby stirring for 10 minutes
  2. stirringwas stirred for 10 minutes
  3. stirringby stirring at -78° C. for 30 minutes
  4. extractionwas extracted with ethyl acetate
  5. washThe extract was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationdistilled
  8. customto remove the solvent

Sources & evidence

ORD record
ord-ddee7f1db0d5492484cffeac0c1a2c12
Source dataset
uspto-grants-1993_02
Patent number
US05189043

Reaction notes

Loading…