Tetrahydrofuran → HCID 131719434, compound

HRID 260239Notes

Reaction equation

HRID 260239 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][CH:10]2[CH2:15][CH2:14][Si:13]([CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:12][CH2:11]2)=[CH:4][CH:3]=1.O1CCCC1.[Cl-].[F:33][C:34]1[CH:35]=[C:36]([Zn+])[CH:37]=[CH:38][C:39]=1[F:40].[Cl-].[NH4+]>C(O)C.[Pt]=O>[CH2:22]([Si:13]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:14][CH2:15][CH:10]([CH2:9][CH2:8][C:5]2[CH:6]=[CH:7][CH:2]=[CH:3][C:4]=2[C:37]2[CH:36]=[CH:35][C:34]([F:33])=[C:39]([F:40])[CH:38]=2)[CH2:11][CH2:12]1)[CH2:23][CH2:24][CH2:25][CH3:26]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 53654974HCID 53654974, compoundHCID 178505908HCID 178505908, compound

Product 1

HCID 131719434HCID 131719434, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

42.8 g of 4-(2-(4-bromophenyl)ethenyl)-1-n-pentyl-1-phenyl-1-silacyclohexane was dissolved in 200 ml of ethanol at room temperature and then hydrogenated at normal pressures in the presence of a catalyst made of 200 mg of platinum oxide. After consumption of a theoretical amount of hydrogen, the catalyst was removed by filtration and the resultant flitrate was concentrated. 200 ml of tetrahydrofuran and 180 mg of tetrakis(triphenylphosphine) palladium (0) were added to the resulting residue. Thereafter, 120 ml of a tetrahydrofuran solution of 1.0 mole of 3,4-difluorophenylzinc chloride, followed by agitation at 40° C. for 12 hours. The reaction mixture was poured into an ammonium chloride aqueous solution and extracted with ethyl acetate. After ordinary washing, drying and concentrating operations, the resultant product was purified through silica gel column chromatography to obtain 39.6 g (yield: 86%) of 4-(2-(4-n-pentyl-4-phenyl-4-silacyclohexyl)ethyl-3',4'-difluorobiphenyl.

Workup

  1. customAfter consumption of a theoretical amount of hydrogen
  2. customthe catalyst was removed by filtration
  3. concentrationthe resultant flitrate was concentrated
  4. addition200 ml of tetrahydrofuran and 180 mg of tetrakis(triphenylphosphine) palladium (0) were added to the resulting residue
  5. extractionextracted with ethyl acetate
  6. customAfter ordinary washing, drying
  7. concentrationconcentrating operations
  8. customthe resultant product was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-8b70a3ed64cb4fa2913de6aa7fa6a8fc
Source dataset
uspto-grants-1996_06
Patent number
US05527490

Reaction notes

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