tert-Butyl methyl ether → HCID 178455736, compound

HRID 2399211Notes

Reaction equation

HRID 2399211 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]#[C:15][C@H:16]3[CH2:21][CH2:20][C@H:19]([CH:22]=O)[CH2:18][CH2:17]3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH3:24]OC(C)(C)C>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:22]([C@H:19]1[CH2:20][CH2:21][C@H:16]([C:15]#[C:14][C:11]2[CH:12]=[CH:13][C:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)=[CH:9][CH:10]=2)[CH2:17][CH2:18]1)=[CH2:24]

Participants

4

Reactant 2

HCID 15413tert-Butyl methyl ether2×HCID 178520938HCID 178520938, compound

Product 1

HCID 178455736HCID 178455736, compound

Reagents, catalysts & solvents 1

HCID 74505Methyltriphenyliphosphonium bromideCatalyst

Procedure

0.73 g of potassium t-butylate was added to a suspension of 2.3 g of methyltriphenylphosphonium bromide in 25 ml of t-butyl methyl ether in a nitrogen atmosphere and the mixture was stirred at room temperature for 0.5 hour. Then, a solution of 0.8 g of trans-4-[(4'-fluoro-4-biphenylyl)ethynyl]cyclohexanecarboxaldehyde in 25 ml of t-butyl methyl ether was added dropwise at 0° C. and the reaction mixture was stirred at 0° C. for a further 0.5 hour and at room temperature for 2.5 hours, thereafter washed with 50 ml of saturated sodium hydrogen carbonate solution and with 50 ml of saturated sodium chloride solution, dried over sodium sulphate, filtered and concentrated. The residue was chromatographed on silica gel with hexane. The 4-[(trans-4-vinylcyclohexyl)ethynyl]-4'-fluorobiphenyl obtained was purified by recrystallization from hexane; m.p. (C-N) 133.9° C., cI.p. (N-I) 170° C.

Workup

  1. stirringthe reaction mixture was stirred at 0° C. for a further 0.5 hour and at room temperature for 2.5 hours
  2. washwashed with 50 ml of saturated sodium hydrogen carbonate solution and with 50 ml of saturated sodium chloride solution
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel with hexane

Sources & evidence

ORD record
ord-80cb8859377346a99a67c3db381b869f
Source dataset
uspto-grants-1995_09
Patent number
US05447657

Reaction notes

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