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

HRID 1195859ノート

反応式

HRID 1195859 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d80a807d0a604008be19e6f600281106
出典データセット
uspto-grants-1992_05
特許番号
US05112853

反応ノート

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