Sulfuric Acid → HCID 19885927, compound

HRID 654894Notes

Reaction equation

HRID 654894 reaction equation
[CH3:1][C:2]([CH3:8])=[CH:3][CH2:4][CH2:5][Mg]Br.[CH3:9][Si:10]([CH3:19])([CH3:18])[C:11]1[O:15][CH:14]=[C:13]([CH:16]=[O:17])[CH:12]=1.S(=O)(=O)(O)O>C(OCC)C>[OH:17][CH:16]([C:13]1[CH:12]=[C:11]([Si:10]([CH3:19])([CH3:18])[CH3:9])[O:15][CH:14]=1)[CH2:5][CH2:4][CH:3]=[C:2]([CH3:8])[CH3:1]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 156632515-(Trimethylsilyl)furan-3-carbaldehydeHCID 178444606HCID 178444606, compound

Product 1

HCID 19885927HCID 19885927, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred solution of 4-methyl-3-pentenylmagnesium bromide (0.74 mmol, prepared from 0.74 mmol 5-bromo-2-methyl-2-pentene and 1.46 mmol magnesium) in two ml anhydrous ethyl ether at 0° under argon was added dropwise 5-trimethylsilyl-3-furaldehyde (0.124 g., 0.74 mmol) in 1.5 ml ethyl ether. This solution was allowed to warm to room temperature, stirred for 30 minutes, and then poured over crushed ice containing several drops of concentrated sulfuric acid. The resulting mixture was partitioned between ethyl ether and 5% sodium bicarbonate. The organic portion was washed with water, saturated sodium chloride, dried over magnesium sulfate, filtered and concentrated to give a colorless oil. This material was purified by flash chromatography (silica, 10% ethyl acetate/hexane) to give the desired alcohol.

Workup

  1. additionpoured
  2. customThe resulting mixture was partitioned between ethyl ether and 5% sodium bicarbonate
  3. washThe organic portion was washed with water, saturated sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a colorless oil
  8. customThis material was purified by flash chromatography (silica, 10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-9a093350165542ec8e1ac750d55a6928
Source dataset
uspto-grants-1992_07
Patent number
US05134128

Reaction notes

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