Water → HCID 17989131, compound

HRID 1444529Notes

Reaction equation

HRID 1444529 reaction equation
C([O:3][C:4](=O)[C:5](=[O:22])[CH2:6][C:7]1([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[C:14]=2[O:20][CH3:21])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)C.[F:24][C:25]([Si](C)(C)C)([F:27])[F:26].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>O1CCCC1.C(OC)(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:19][C:15]1[C:14]([O:20][CH3:21])=[C:13]([C:7]2([CH2:6][C:5]([OH:22])([C:25]([F:27])([F:26])[F:24])[CH:4]=[O:3])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:18]=[CH:17][CH:16]=1

Participants

8

Reactant 4

HCID 962WaterHCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 17989207HCID 17989207, compound

Product 1

HCID 17989131HCID 17989131, compoundYield 51.1%

Reagents, catalysts & solvents 3

HCID 2724141Tetrabutylammonium FluorideCatalystHCID 8028TetrahydrofuranSolvent2×HCID 15413tert-Butyl methyl etherSolvent

Procedure

7.07 g (20.87 mmol) of ethyl-3-[1-(3-chloro-2-methoxyphenyl)-cyclohexyl]-2-oxopropionate is dissolved in 33 ml of tetrahydrofuran and mixed with 3.56 g (25.04 mmol) of (trifluoromethyl)-trimethylsilane. After 51.1 mg of tetrabutylammonium fluoride is added, the batch is stirred overnight. The reaction mixture is diluted with methyl tert-butyl ether, washed once with water and then with brine. After conventional working-up, the residue is chromatographed on silica gel (mobile solvent ethyl acetate/hexane). The isolated 5.71 g (60.4%) of the product is mixed in 70 ml of tetrahydrofuran with 3.98 g (12.61 mmol) of tetrabutylammonium fluoride and stirred for one hour at room temperature. After the reaction mixture is mixed with water, it is extracted with methyl tert-butyl ether. After conventional working-up, the residue is chromatographed on a Flashmaster. 2.63 g (51.1%) of the desired compound: ethyl-2-[1-(3-chloro-2-methoxyphenyl)-cyclohexylmethyl]-3,3,3-trifluoro-2-hydroxypropionate is isolated.

Workup

  1. washwashed once with water
  2. customAfter conventional working-up, the residue is chromatographed on silica gel (mobile solvent ethyl acetate/hexane)
  3. stirringstirred for one hour at room temperature
  4. extractionis extracted with methyl tert-butyl ether
  5. customAfter conventional working-up, the residue is chromatographed on a Flashmaster

Sources & evidence

ORD record
ord-b8e72e639f2d4bd6b9fd2473e74f20f5
Source dataset
uspto-grants-2010_02
Patent number
US07662821B2

Reaction notes

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