Tetrahydrofuran → 4-(12-t-Butyldimethylsiloxy-1-hydroxydodecyl)-2-trimethylsilylfuran

HRID 654953Notes

Reaction equation

HRID 654953 reaction equation
[Mg].Br[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16].[CH3:22][Si:23]([C:26]1[O:27][CH:28]=[CH:29][C:30]=1C=O)([CH3:25])[CH3:24].[O:33]1CCC[CH2:34]1>>[O:14]([CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH:34]([C:29]1[CH:30]=[C:26]([Si:23]([CH3:22])([CH3:24])[CH3:25])[O:27][CH:28]=1)[OH:33])[Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran4×HCID 5462224MagnesiumHCID 150371652-(Trimethylsilyl)furan-3-carbaldehydeHCID 15086119[(11-Bromoundecyl)oxy](tert-butyl)dimethylsilane

Product 1

HCID 198859754-(12-t-Butyldimethylsiloxy-1-hydroxydodecyl)-2-trimethylsilylfuran

Procedure

To a stirred suspension of magnesium turnings (0.142 g, 5.9 mmol) in tetrahydrofuran (1 ml) at room temperature under nitrogen was added a solution of 1-bromo-11-t-butyldimethylsiloxyundecane (1.06 g, 2.9 mmol) in tetrahydrofuran (1.5 ml). This mixture was heated to reflux and stirred for 1 hour, then cooled to 0° and diluted with tetrahydrofuran (3 ml). Trimethylsilyl-3-furanaldehyde (0.491 g, 2.9 mmol) was added dropwise in 2 ml of tetrahydrofuran. The solution was stirred for 1 hour at 0°, 4.5 hours at room temperature, quenched with saturated ammonium chloride solution and poured into ethyl ether. The organic portion was washed twice with water, once with saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated to give a yellow liquid. The alcohol (Rf =0.33, 20% ethyl ether/hexane) was purified by flash chromatography (silica, 10-15% ethyl ether/petroleum ether) to give a pale oil.

Workup

  1. temperatureThis mixture was heated
  2. temperatureto reflux
  3. temperaturecooled to 0°
  4. stirringThe solution was stirred for 1 hour at 0°, 4.5 hours at room temperature
  5. customquenched with saturated ammonium chloride solution
  6. additionpoured into ethyl ether
  7. washThe organic portion was washed twice with water, once with saturated sodium chloride solution
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customto give a yellow liquid
  12. customThe alcohol (Rf =0.33, 20% ethyl ether/hexane) was purified by flash chromatography (silica, 10-15% ethyl ether/petroleum ether)
  13. customto give a pale oil

Sources & evidence

ORD record
ord-78fa332c916c46c5b96f1e04d75dd26d
Source dataset
uspto-grants-1992_07
Patent number
US05134128

Reaction notes

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