Ethyl trifluoroacetate → HCID 2853017, compound

HRID 1013019Notes

Reaction equation

HRID 1013019 reaction equation
[H-].[Na+].[F:3][C:4]([F:11])([F:10])[C:5]([O:7]CC)=O.[C:12]1(/[CH:18]=[CH:19]/[C:20](=[O:22])[CH3:21])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[F:11][C:4]([F:3])([F:10])[C:5](=[O:7])[CH2:21][C:20](=[O:22])[CH:19]=[CH:18][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 3

HCID 9794Ethyl trifluoroacetate2×HCID 24758Sodium hydride2×HCID 637759Benzylideneacetone

Product 1

HCID 2853017HCID 2853017, compound

Conditions

Temperature
40 °C

Procedure

Sodium hydride (547 mg, 60% dispersion in mineral oil, 13.68 mmol) was added to ethyl trifluoroacetate (1.63 mL, 13.68 mmol). (Note: Carefulness is required. The reaction caught fire upon adding sodium hydride to ethyl trifluoroacetate.) Trans-4-Phenyl-3-buten-2-one (1 g, 6.84 mmol) was added, and the reaction was stirred for 3 hours at 40° C. The reaction was cooled to room temperature and quenched with water, then diluted with 1 N HCl. The mixture was extracted with ethyl acetate, dried over MgSO4, and concentrated. The reaction was assumed to be quantitative. LC-MS (C12H9F3O2 calculated 242) m/z 243 (M+H).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. customquenched with water
  3. additiondiluted with 1 N HCl
  4. extractionThe mixture was extracted with ethyl acetate
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-78f6c26a423f4e87a618059cc4e5125b
Source dataset
uspto-grants-2011_07
Patent number
US07981896B2

Reaction notes

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