Hexane → HCID 54297396, compound

HRID 414275Notes

Reaction equation

HRID 414275 reaction equation
C([Li])CCC.[Br-].[F:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:10][C:9]=1[O:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.[CH3:42][O:43][C:44]1[CH:49]=[CH:48][C:47]([C:50]([C:54]([F:57])([F:56])[F:55])([CH3:53])[CH:51]=O)=[CH:46][CH:45]=1.[CH3:58][CH2:59][CH2:60][CH2:61][CH2:62]C>O1CCCC1>[F:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH:15]=[CH:51][C:50]([C:47]2[CH:48]=[CH:49][C:44]([O:43][C:42]3[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=3)=[CH:45][CH:46]=2)([C:54]([F:57])([F:56])[F:55])[CH3:53])=[CH:10][C:9]=1[O:35][C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 13885602HCID 13885602, compoundHCID 21252173[2-(4-Fluoro-3-phenoxyphenyl)ethyl](triphenyl)phosphanium bromideHCID 178418339Butyllithium

Product 1

HCID 54297396HCID 54297396, compoundYield 80.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of butyllithium in hexane (1.6 molar; 30 ml) was added, dropwise, under a nitrogen atmosphere to [2-(4-fluoro-3-phenoxyphenyl)ethyl]triphenylphosphonium bromide (26.76 g; 48 mmol) in absolute tetrahydrofuran (200 ml). After stirring for two hours, 2-(4-methoxyphenyl)-2-trifluoromethylpropionaldehyde (10.13 g; 43.63 mmol) dissolve in absolute tetrahydrofuran (80 ml) was added, dropwise. The mixture was heated at reflux for 3 hours and then added to ice-water, extracted with ethyl acetate, the extract dried over sodium sulphate and evaporated. After chromatography on silica gel using hexane/ethyl acetate as eluent, there was obtained 1-(4-fluoro-3-phenoxyphenyl)-4-(4-phenoxyphenyl)-4-trifluoromethyl-2-pentene (15.2 g=80.5% of theory).

Workup

  1. additionwas added
  2. temperatureThe mixture was heated
  3. temperatureat reflux for 3 hours
  4. extractionextracted with ethyl acetate
  5. dry with materialthe extract dried over sodium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-05098ff2fac840dab2665b1c6e9b483b
Source dataset
uspto-grants-1988_12
Patent number
US04791123

Reaction notes

Loading…