2,2,2-Trifluoroacetophenone → HCID 54173602, compound

HRID 414280Notes

Reaction equation

HRID 414280 reaction equation
C([Li])CCC.[Br-].[O:7]([C:14]1[CH:15]=[C:16]([CH2:20][CH2:21][CH2:22][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:17]=[CH:18][CH:19]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[F:42][C:43]([F:53])([F:52])[C:44]([C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)=O>CCCCCC.O1CCCC1>[O:7]([C:14]1[CH:15]=[C:16]([CH2:20][CH2:21][CH:22]=[C:44]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[C:43]([F:52])([F:42])[F:53])[CH:17]=[CH:18][CH:19]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 99052,2,2-TrifluoroacetophenoneHCID 21274172HCID 21274172, compoundHCID 178418339Butyllithium

Product 1

HCID 54173602HCID 54173602, compoundYield 71.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

A solution of butyllithium in n-hexane (8.5 ml of 1.6 molar) was added, dropwise, at room temperature and under a nitrogen atmosphere over 10 minutes to [3-(3-phenoxyphenyl)propyl]-triphenylphophonium bromide (7.67 g; 13.75 mmol) in absolute tetrahydrofuran (40 ml). After stirring for 2 hours, α,α,α-trifluoroacetophenone (2.18 g; 12.5 mmol) dissolved in absolute tetrahydrofuran (10 ml) was added dropwise. After stirring for 3 hours at room temperature, the mixture was added to ice-water, extracted with ether and the extract dried over sodium sulphate and evaporated. After chromotography on silica gel using hexane-toluene, there was obtained 4-(3-phenoxyphenyl)-1-phenyl-1-trifluoromethyl-1-butene (3.31 g=71.9% of theory).

Workup

  1. additionwas added dropwise
  2. stirringAfter stirring for 3 hours at room temperature
  3. extractionextracted with ether
  4. dry with materialthe extract dried over sodium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-361abcd67e674e77ac2729d7ad680e9d
Source dataset
uspto-grants-1988_12
Patent number
US04791123

Reaction notes

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