Sulfuric Acid → HCID 19885895, compound

HRID 654902Notes

Reaction equation

HRID 654902 reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[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>O1CCCC1>[OH:17][CH:16]([C:13]1[CH:12]=[C:11]([Si:10]([CH3:19])([CH3:18])[CH3:9])[O:15][CH:14]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 156632515-(Trimethylsilyl)furan-3-carbaldehydeHCID 178418255HCID 178418255, compound

Product 1

HCID 19885895HCID 19885895, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of phenylmagnesium bromide (0.41 ml, 1.27 mmol, 3.1M solution in ethyl ether) under argon at 0°, was added dropwise 5-trimethylsilyl-3-furaldehyde (0.194 g., 1.15 mmol) in 2 ml tetrahydrofuran. This solution was allowed to warm to room temperature, stirred for 30 minutes, and 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 solution, 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 solution
  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-b599db2551464603b415646928beddc8
Source dataset
uspto-grants-1992_07
Patent number
US05134128

Reaction notes

Loading…