Pyridine → 4-Dodecoyloxymethyl-2-trimethylsilylfuran

HRID 654918Notes

Reaction equation

HRID 654918 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([Si:8]([CH3:11])([CH3:10])[CH3:9])[O:6][CH:7]=1.N1C=CC=CC=1.[C:18](Cl)(=[O:30])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]>O1CCCC1>[C:18]([O:1][CH2:2][C:3]1[CH:4]=[C:5]([Si:8]([CH3:11])([CH3:10])[CH3:9])[O:6][CH:7]=1)(=[O:30])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

Participants

5

Reactant 3

HCID 1049PyridineHCID 8166Dodecanoyl chlorideHCID 13333558(2-Trimethylsilyl-4-furyl)methanol

Product 1

HCID 150370464-Dodecoyloxymethyl-2-trimethylsilylfuran

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 4-hydroxymethyl-2-trimethylsilylfuran (0.288 g., 1.70 mmol) and pyridine (0.214 g., 2.55 mmol) in 30 ml dry tetrahydrofuran at 0° was added lauroyl chloride (0.408 g., 1.86 mmol). This solution was allowed to warm to room temperature, stirred 30 minutes, and partitioned between ethyl ether and 5% sodium bicarbonate solution. The organic portion was washed with aqueous cupric sulfate solution, water, saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated to a colorless oil. This material was purified by flash chromatography (silica, 5% ethyl ether/petroleum ether) to give the desired ester.

Workup

  1. custompartitioned between ethyl ether and 5% sodium bicarbonate solution
  2. washThe organic portion was washed with aqueous cupric sulfate solution, water, saturated sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to a colorless oil
  6. customThis material was purified by flash chromatography (silica, 5% ethyl ether/petroleum ether)

Sources & evidence

ORD record
ord-3101aeadfe724ac5a465f4eed5280e48
Source dataset
uspto-grants-1992_07
Patent number
US05134128

Reaction notes

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