Methyl acetoacetate → HCID 14459258, compound

HRID 1074172Notes

Reaction equation

HRID 1074172 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]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:25](=[O:33])[N:26]([CH3:32])[C:27]=2/[CH:28]=[CH:29]/[CH:30]=[O:31])=[CH:19][CH:18]=1.[Cl-].[NH4+]>O1CCCC1.CCCCCC.[Br-].[Zn+2].[Br-]>[F:16][C:17]1[CH:18]=[CH:19][C:20]([C:23]2[N:24]([C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)[C:25](=[O:33])[N:26]([CH3:32])[C:27]=2/[CH:28]=[CH:29]/[CH:30]([OH:31])[CH2:5][C:3](=[O:4])[CH2:2][C:1]([O:7][CH3:8])=[O:6])=[CH:21][CH:22]=1

Participants

9

Reactant 5

HCID 7757Methyl acetoacetateHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 14459257HCID 14459257, compoundHCID 178418339Butyllithium

Product 1

HCID 14459258HCID 14459258, compound

Reagents, catalysts & solvents 3

HCID 10421208Zinc bromideCatalystHCID 8028TetrahydrofuranSolvent3×HCID 8058HexaneSolvent

Procedure

0.59 ml (5.4 mmol) of methyl acetoacetate is added dropwise under nitrogen to a suspension of 135 mg (5.6 mmol) of sodium hydride in 14 ml of tetrahydrofuran at -5° C. After 15 minutes, 4.0 ml (5.6 mmol) of 15% strength n-butyllithium in n-hexane are added dropwise at -5° C. the mixture is stirred for 15 minutes, a solution of 1.3 g (5.9 mmol) of zinc bromide in 20 ml of THF is added, the mixture is stirred for 15 minutes and a solution of 0.6 g (1.8 mmol) of the compound from Example 5 in 6 ml of tetrahydrofuran is added. After 30 minutes at -5° C., the mixture is hydrolyzed using saturated ammonium chloride solution, washed three times with dichloromethane, and the organic phase is dried and 380 mg are obtained after removing the solvent and washing the residue with petroleum ether.

Workup

  1. stirringthe mixture is stirred for 15 minutes
  2. waitAfter 30 minutes at -5° C.
  3. washwashed three times with dichloromethane
  4. customthe organic phase is dried
  5. custom380 mg are obtained
  6. customafter removing the solvent
  7. washwashing the residue with petroleum ether

Sources & evidence

ORD record
ord-8296d4b511c742bca99f3fa3fe1af5fc
Source dataset
uspto-grants-1990_11
Patent number
US04973598

Reaction notes

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