Sulfuric Acid → HCID 19885935, compound

HRID 654901Notes

Reaction equation

HRID 654901 reaction equation
[CH:1]1([Mg]Cl)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]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>[CH:1]1([CH:16]([C:13]2[CH:12]=[C:11]([Si:10]([CH3:19])([CH3:18])[CH3:9])[O:15][CH:14]=2)[OH:17])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 156632515-(Trimethylsilyl)furan-3-carbaldehydeHCID 178478990HCID 178478990, compound

Product 1

HCID 19885935HCID 19885935, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of cyclohexylmagnesium chloride (0.24 ml, 0.484 mmol, 2.0M solution in ethyl ether) under argon at 0°, was added dropwise 5-trimethylsilyl-3-furaldehyde (0.072 g., 0.44 mmol) in 5 ml of dry 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 ether/pentane) to yield 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 ether/pentane)

Sources & evidence

ORD record
ord-da1daa23dd284d938e46f9bc6a22e000
Source dataset
uspto-grants-1992_07
Patent number
US05134128

Reaction notes

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