Boron trifluoride etherate → 5-Hydroxy-2-(4-methyl-3-pentenyl)-5-(2-trimethylsilyl-4-furyl)-2-pentenal

HRID 256618Notes

Reaction equation

HRID 256618 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]([CH3:35])=[CH:23][CH2:24][CH2:25][C:26]([CH:33]=[CH2:34])=[CH:27][O:28][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)[CH2:34][CH:33]=[C:26]([CH2:25][CH2:24][CH:23]=[C:22]([CH3:21])[CH3:35])[CH:27]=[O:28]

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 156632515-(Trimethylsilyl)furan-3-carbaldehydeHCID 537963512-(4-Methyl-3-pentenyl)-1-trimethylsilyloxy-1,3-butadiene

Product 1

HCID 572176475-Hydroxy-2-(4-methyl-3-pentenyl)-5-(2-trimethylsilyl-4-furyl)-2-pentenal

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 5-trimethylsilyl-3-furanaldehyde (0.444 g, 2.6 mmol) in 5 ml methylene chloride at -60° under argon was added dropwise boron trifluoride etherate (0.33 ml, 2.7 mmol). After one to two minutes a solution of 2-(4-methyl-3-pentenyl)-1-trimethylsilyloxy-1,3-butadiene (0.604 g, 2.7 mmol) in 3 ml methylene chloride was added dropwise. The solution was stirred for 20 hours at -60°, quenched with saturated sodium bicarbonate solution, warmed to room temperature, and taken up in ethyl ether. The organic portion was washed twice with saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated to give an orange oil which was complex by TLC. The mixture was purified by flash chromatography (silica, 30% ethyl acetate/hexane). Eluted last was the desired hydroxyaldehyde as an orange oil.

Workup

  1. customquenched with saturated sodium bicarbonate solution
  2. washThe organic portion was washed twice with saturated sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give an orange oil which
  7. customThe mixture was purified by flash chromatography (silica, 30% ethyl acetate/hexane)
  8. washEluted last

Sources & evidence

ORD record
ord-10db8e9883ce4229b27149ec323919ad
Source dataset
uspto-grants-1993_11
Patent number
US05258400

Reaction notes

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