5-(Trimethylsilyl)furan-3-carbaldehyde → HCID 19885958, compound

HRID 654934Notes

Reaction equation

HRID 654934 reaction equation
[C:1]1([CH2:7][CH2:8]/[CH:9]=[CH:10]/[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:18][Si:19]([CH3:28])([CH3:27])[C:20]1[O:24][CH:23]=[C:22]([CH:25]=[O:26])[CH:21]=1>O1CCCC1>[OH:26][CH:25]([C:22]1[CH:21]=[C:20]([Si:19]([CH3:28])([CH3:27])[CH3:18])[O:24][CH:23]=1)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]/[CH:10]=[CH:9]/[CH2:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 156632515-(Trimethylsilyl)furan-3-carbaldehydeHCID 178419679HCID 178419679, compound

Product 1

HCID 19885958HCID 19885958, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of (E)-9-phenylnon-6-enyl magnesium bromide (0.861 mmol, prepared from 0.242 g, 0.861 mmol, of (E)-1-bromo-9-phenylnon-6-ene and 2.88 mmol magnesium) in tetrahydrofuran (10 ml) at 0° under argon was added dropwise, 5-trimethylsilyl-3-furaldehyde (0.145 g, 0.861 mmol) in tetrahydrofuran (5 ml). The solution was warmed to room temperature, stirred for 5 hours, quenched with 5% ammonium chloride and extracted into ethyl ether. The organic portion was washed with 5% sodium bicarbonate, water, saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated to give yellow oil. Purification by flash chromatography (silica, 5 to 20% ethyl acetate/hexane) gave the desired alcohol.

Workup

  1. customquenched with 5% ammonium chloride
  2. extractionextracted into ethyl ether
  3. washThe organic portion was washed with 5% sodium bicarbonate, water, saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give yellow oil
  8. customPurification by flash chromatography (silica, 5 to 20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-39d623e964834b6eae73f14acf1465dd
Source dataset
uspto-grants-1992_07
Patent number
US05134128

Reaction notes

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