Ethyl 4,4,4-trifluoroacetoacetate → HCID 9965592, compound

HRID 459710Notes

Reaction equation

HRID 459710 reaction equation
COC1[CH:13]=[CH:12][C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][NH:11][C:5]=2C=1.[F:14][C:15]([F:25])([F:24])[C:16](=O)[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19]>[Cl-].[Zn+2].[Cl-].CCO>[F:14][C:15]([F:25])([F:24])[C:16]1[C:13]2[C:21](=[CH:22][C:5]3[NH:11][CH2:10][CH2:9][CH2:8][CH2:7][C:6]=3[CH:12]=2)[O:20][C:18](=[O:19])[CH:17]=1

Participants

5

Reactant 2

HCID 67793Ethyl 4,4,4-trifluoroacetoacetateHCID 16244477HCID 16244477, compound

Product 1

HCID 9965592HCID 9965592, compound

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

Equimolar amounts of 8-methoxy-2,3,4,5-tetrahydro-1H-1-benzazepine 1-4 (0.18 g, 1.12 mmol), ethyl 4,4,4-trifluoroacetoacetate (0.205 g, 1.12 mmol), and zinc chloride (1.12 mL, 1M solution in Et2O) were combined in a pressure bottle with 10 mL absolute EtOH. The bottle was sealed and allowed to stir at 100° C. for overnight. The reaction darkened from a clear and colorless solution to a dark green solution. After cooling to rt, the reaction solution was absorbed onto silica gel and purified on an ISCO automated system affixed with a BIOTAGE flash 40(S) cartridge eluting 5–25% EtOAc in hexane to provide the desired product 1-5. Data for 1-5: HRMS Calcd (M+1) 284.0893; found 284.0901.

Workup

  1. customThe bottle was sealed
  2. temperatureAfter cooling to rt
  3. customthe reaction solution was absorbed onto silica gel
  4. custompurified on an ISCO automated system
  5. washeluting 5–25% EtOAc in hexane

Sources & evidence

ORD record
ord-51f79a91b51d4a2793f524f796b60385
Source dataset
uspto-grants-2007_03
Patent number
US07196076B2

Reaction notes

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