Boron trifluoride etherate → 5-Hydroxy-2-methyl-5-(2-trimethylsilylfuran-4-yl)-2-pentenal

HRID 1195856Notes

Reaction equation

HRID 1195856 reaction equation
[CH3:1][Si:2]([CH3:11])([CH3:10])[C:3]1[O:7][CH:6]=[C:5]([CH:8]=[O:9])[CH:4]=1.B(F)(F)F.CCOCC.[CH3:21][C:22]([CH:29]=[CH2:30])=[CH:23][O:24][Si](C)(C)C>C(Cl)Cl>[OH:9][CH:8]([C:5]1[CH:4]=[C:3]([Si:2]([CH3:11])([CH3:10])[CH3:1])[O:7][CH:6]=1)[CH2:30][CH:29]=[C:22]([CH3:21])[CH:23]=[O:24]

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 1791012-Methyl-1-trimethylsilyloxy-1,3-butadieneHCID 156632515-(Trimethylsilyl)furan-3-carbaldehyde

Product 1

HCID 572938505-Hydroxy-2-methyl-5-(2-trimethylsilylfuran-4-yl)-2-pentenal

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 5-trimethylsilyl-3-furaldehyde (0.382 g., 2.27 mmol) in dry methylene chloride (15 ml) at -50° under argon was added dropwise boron trifloride etherate (0.28 ml, 2.3 mmol). This addition was followed by the dropwise addition of 2-methyl-1-trimethylsilyloxy-1,3-butadiene (0.356 g., 2.3 mmol). The solution was stirred at -50° to -60° for 18 hours, quenched by the addition of several ml saturated sodium bicarbonate solution, warmed to room temperature and poured into methylene chloride. The organic portion was washed once with saturated bicarbonate solution, once with water, once with saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated to give a yellow oil which consisted of several components by TLC. The mixture was applied to a chromatography column (silica) and eluted with 30% ethyl acetate/hexane. Eluted last was the desired alcohol, which was concentrated to give a yellow gum.

Workup

  1. additionThis addition
  2. customquenched by the addition of several ml saturated sodium bicarbonate solution
  3. additionpoured into methylene chloride
  4. washThe organic portion was washed once with saturated bicarbonate solution, once with water, once with saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a yellow oil which
  9. washeluted with 30% ethyl acetate/hexane
  10. washEluted last
  11. concentrationwas concentrated
  12. customto give a yellow gum

Sources & evidence

ORD record
ord-69d1fe291f204e00b0a6c224f4787f3c
Source dataset
uspto-grants-1992_05
Patent number
US05112853

Reaction notes

Loading…