Ethyl Acetate → HCID 86715647, compound

HRID 1507294Notes

Reaction equation

HRID 1507294 reaction equation
[H-].[Na+].[O:3]=[C:4]([CH2:11][CH3:12])[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7].[F:13][C:14]([F:24])([F:23])[C:15]1[CH:22]=[CH:21][C:18]([CH2:19]Br)=[CH:17][CH:16]=1.C(OCC)(=O)C>C(COC)OC.O>[O:3]=[C:4]([CH2:11][CH3:12])[CH:5]([CH2:19][C:18]1[CH:17]=[CH:16][C:15]([C:14]([F:13])([F:23])[F:24])=[CH:22][CH:21]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 78656Ethyl 3-oxovalerateHCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzene

Product 1

HCID 86715647HCID 86715647, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent2×

Procedure

Sodium hydride (60% dispersion in mineral oil, 1.75 g, 43.7 mmol) was added in portions over 1 minute to an ice-cooled, stirring solution of ethyl 3-oxopentanoate (6.30 g, 43.7 mmol) in dry dimethoxyethane (87 mL). After 5 minutes, the flask was removed from the cooling bath and stirring continued at room temperature. After 30 minutes, a solution of 4-(trifluoromethyl)benzyl bromide (10.4 g, 43.7 mmol) in dry dimethoxyethane (10 mL) was added dropwise over 2 minutes. After 2.5 hours, ethyl acetate (300 mL) and water (100 mL) were added. The layers were separated. The organic layer was dried with sodium sulfate and the dried solution was filtered. The filtrate was concentrated and the residue was purified by flash-column chromatography on silica gel eluting with hexanes initially, grading to 50% dichloromethane-hexanes to provide the title compound as a colorless liquid.

Workup

  1. temperaturecooled
  2. customthe flask was removed from the cooling bath
  3. customcontinued at room temperature
  4. waitAfter 30 minutes
  5. waitAfter 2.5 hours
  6. customThe layers were separated
  7. dry with materialThe organic layer was dried with sodium sulfate
  8. filtrationthe dried solution was filtered
  9. concentrationThe filtrate was concentrated
  10. customthe residue was purified by flash-column chromatography on silica gel eluting with hexanes initially

Sources & evidence

ORD record
ord-013fe9b6323c42cd9203ed133617b5b0
Source dataset
uspto-grants-2015_12
Patent number
US09221804B2

Reaction notes

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