(Trifluoromethyl)trimethylsilane → HCID 17989248, compound

HRID 1443159Notes

Reaction equation

HRID 1443159 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[C:5](=[O:19])[CH2:6][C:7]([C:10]1[C:18]2[O:17][CH2:16][O:15][C:14]=2[CH:13]=[CH:12][CH:11]=1)([CH3:9])[CH3:8])[CH3:2].[F:21][C:22]([Si](C)(C)C)([F:24])[F:23].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.C(OCC)(=O)C.CCCCCC>[CH2:1]([O:3][C:4](=[O:20])[C:5]([OH:19])([C:22]([F:24])([F:23])[F:21])[CH2:6][C:7]([C:10]1[C:18]2[O:17][CH2:16][O:15][C:14]=2[CH:13]=[CH:12][CH:11]=1)([CH3:9])[CH3:8])[CH3:2]

Participants

6

Reactant 3

HCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 17989302Ethyl γ,γ-dimethyl-α-oxo-1,3-benzodioxole-4-butanoate2×

Product 1

HCID 17989248HCID 17989248, compoundYield 215.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 21226206Ethyl acetate hexaneSolvent

Procedure

6.1 g (21.91 mmol) of 4-(1,3-benzodioxol-4-yl)-4-methyl-2-oxopentanoic acid ethyl ester, dissolved in 130 ml of tetrahydrofuran, is reacted with 9.5 ml (65.7 mmol) of (trifluoromethyl)trimethylsilane and 4.42 ml of a 1 M solution of tetrabutylammonium fluoride in tetrahydrofuran. Carrying out and working up the reaction are carried out as described in Example 3. The crude product that is obtained is purified together with one batch of a similar order of magnitude [9.19 g (33.02 mmol) of 4-(1,3-benzodioxol-4-yl)-4-methyl-2-oxopentanoic acid ethyl ester as a starting material] by chromatography on silica gel (mobile solvent:ethyl acetate/hexane). 16.45 g (86%) of the desired product is isolated from the two batches together.

Workup

  1. customThe crude product that is obtained

Sources & evidence

ORD record
ord-185c263381d84bb09c5fea47eafc1534
Source dataset
uspto-grants-2010_02
Patent number
US07659297B2

Reaction notes

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