Water → HCID 86760516, compound

HRID 1295610Notes

Reaction equation

HRID 1295610 reaction equation
[I-].[CH:2]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([CH3:4])[CH3:3].C([Li])CCC.[F:29][C:30]([F:44])([F:43])[C:31]1[CH:32]=[C:33]([CH:36]=[C:37]([C:39]([F:42])([F:41])[F:40])[CH:38]=1)[CH:34]=O.O>C(OCC)C.O1CCCC1.CCCCCC.O1CCCC1>[CH3:3][C:2]([CH3:4])=[CH:34][C:33]1[CH:32]=[C:31]([C:30]([F:44])([F:43])[F:29])[CH:38]=[C:37]([C:39]([F:42])([F:41])[F:40])[CH:36]=1

Participants

8

Reactant 4

HCID 962WaterHCID 1362473,5-Bis(trifluoromethyl)benzaldehydeHCID 2723783Isopropyltriphenylphosphonium iodideHCID 178418339Butyllithium

Product 1

HCID 86760516HCID 86760516, compound

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent2×HCID 21868444Ether tetrahydrofuranSolvent

Conditions

Temperature
-10 °C

Procedure

15.88 g (36 mmol) isopropyltriphenylphosphonium iodide are dissolved in 210 mL diethyl ether/tetrahydrofuran (1:1) and cooled to −10° C. At this temperature 25 mL of a 1.6 molar solution of butyllithium in hexane are added dropwise. Then the mixture is stirred for 3 h at ambient temperature and then cooled to −50° C. 9.98 g (40 mmol) of 3,5-bis-trifluoromethyl-benzaldehyde dissolved in 15 ml of tetrahydrofuran are added dropwise and the mixture is stirred overnight while heating to ambient temperature. The reaction mixture is combined with water and hexane, stirred for 30 minutes and then filtered. The organic phase is separated off, washed repeatedly with water, dried with sodium sulphate and evaporated down. The residue is purified by chromatography on a short silica gel column (hexane/ethyl acetate=50:1). Yellow oil.

Workup

  1. temperaturecooled to −50° C
  2. additionare added dropwise
  3. stirringthe mixture is stirred overnight
  4. temperaturewhile heating to ambient temperature
  5. stirringstirred for 30 minutes
  6. filtrationfiltered
  7. customThe organic phase is separated off
  8. washwashed repeatedly with water
  9. dry with materialdried with sodium sulphate
  10. customevaporated down
  11. customThe residue is purified by chromatography on a short silica gel column (hexane/ethyl acetate=50:1)

Sources & evidence

ORD record
ord-1d5b554796a04c82b9b0faaae077d29f
Source dataset
uspto-grants-2007_07
Patent number
US07244728B2

Reaction notes

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