Acetone → Ethyl 4-oxo-2-(2,2,2-trifluoroacetyl)pentanoate

HRID 1654118Notes

Reaction equation

[F:1][C:2]([F:12])([F:11])[C:3](=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[H-].[Na+].[CH3:15][C:16]([CH3:18])=[O:17].ClCC(=O)C>O1CCCC1.[I-].[K+]>[O:17]=[C:16]([CH3:18])[CH2:15][CH:4]([C:3](=[O:10])[C:2]([F:11])([F:12])[F:1])[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

Conditions

Temperature: 20 °C

Procedure

36.8 g of ethyl 4,4,4-trifluoroacetoacetate were mixed in 400 ml of tetrahydrofuran and 9.6 g of sodium hydride were added at 15° C. over 30 minutes. The mixture was stirred at 20° C. for 1 hour and 0.4 g of potassium iodide and 100 ml of acetone were added. 21 g of chloroacetone in 75 ml of tetrahydrofuran were added dropwise over 15 minutes and the mixture was refluxed for 96 hours and then distilled to obtain 24.4 g of the expected product with a boiling point of 65° C. (0.2 mbar).

Workup

temperaturethe mixture was refluxed for 96 hours
distillationdistilled

Sources & evidence

ORD record: ord-d1095c1ee73041f9955c22b7a888526d
Source dataset: uspto-grants-1995_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05405865

Reaction notes

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