Water → HCID 17989145, compound

HRID 1869444Notes

Reaction equation

HRID 1869444 reaction equation
C(O[C:4](=[O:20])[C:5](=[O:19])[CH2:6][C:7]1([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[C:11]=2[O:17][CH3:18])[CH2:9][CH2:8]1)C.[F:21][C:22]([Si](C)(C)C)([F:24])[F:23].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>O1CCCC1.C(OC)(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:16][C:12]1[C:11]([O:17][CH3:18])=[C:10]([C:7]2([CH2:6][C:5]([OH:19])([C:22]([F:24])([F:23])[F:21])[CH:4]=[O:20])[CH2:8][CH2:9]2)[CH:15]=[CH:14][CH:13]=1

Participants

8

Reactant 4

HCID 962WaterHCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 17989191HCID 17989191, compound

Product 1

HCID 17989145HCID 17989145, compoundYield 47.4%

Reagents, catalysts & solvents 3

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

Procedure

6.18 g (20.83 mmol) of ethyl-3-[1-(3-chloro-2-methoxyphenyl)-cyclopropyl]-2-oxopropionate is dissolved in 33 ml of tetrahydrofuran and mixed with 3.55 g (24.99 mmol) of (trifluoromethyl)-trimethylsilane. After 51 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 5.65 g (66.4%) of product is mixed in 76 ml of tetrahydrofuran with 4.34 g (13.75 mmol) of tetrabutylammonium fluoride, and it is 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. 2.39 g (47.4%) of the desired compound: ethyl-2-[1-(3-chloro-2-methoxyphenyl)-cyclopropylmethyl]-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. stirringis stirred 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-9eac5d0c2c1f4293bdb0080c1cc605db
Source dataset
uspto-grants-2009_12
Patent number
US07638515B2

Reaction notes

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